multiple media upload and smartphone preview

config/migrate_add_media_items.sql

@@ -0,0 +1,27 @@
+-- Migration: Add multi-media support to generated_posts
+-- Date: 2026-02-11
+-- Description: Adds media_items JSONB array to support up to 3 images or 1 video per post
+
+-- Add media_items column
+ALTER TABLE generated_posts ADD COLUMN IF NOT EXISTS media_items JSONB DEFAULT '[]'::JSONB;
+
+-- Add GIN index for performance on JSONB queries
+CREATE INDEX IF NOT EXISTS idx_generated_posts_media_items ON generated_posts USING GIN (media_items);
+
+-- Migrate existing image_url to media_items array
+UPDATE generated_posts
+SET media_items = jsonb_build_array(
+    jsonb_build_object(
+        'type', 'image',
+        'url', image_url,
+        'order', 0,
+        'content_type', 'image/jpeg',
+        'uploaded_at', NOW()
+    )
+)
+WHERE image_url IS NOT NULL AND media_items = '[]'::JSONB;
+
+-- Note: image_url column is kept for backward compatibility
+-- New code should use media_items, but existing code still works
+
+COMMENT ON COLUMN generated_posts.media_items IS 'JSONB array of media items (images/videos). Max 3 items. Structure: [{type, url, order, content_type, uploaded_at, metadata}]';

src/database/models.py

@@ -1,5 +1,5 @@
 """Pydantic models for database entities."""
-from datetime import datetime, date
+from datetime import datetime, date, timezone
 from enum import Enum
 from typing import Optional, Dict, Any, List
 from uuid import UUID
@@ -312,6 +312,16 @@ class ApiUsageLog(DBModel):
     created_at: Optional[datetime] = None
 
 
+class MediaItem(BaseModel):
+    """Single media item (image or video) for a post."""
+    type: str  # "image" | "video"
+    url: str
+    order: int
+    content_type: str  # MIME type (e.g., 'image/jpeg', 'video/mp4')
+    uploaded_at: datetime = Field(default_factory=lambda: datetime.now(timezone.utc))
+    metadata: Optional[Dict[str, Any]] = None
+
+
 class GeneratedPost(DBModel):
     """Generated post model."""
     id: Optional[UUID] = None
@@ -327,7 +337,9 @@ class GeneratedPost(DBModel):
     approved_at: Optional[datetime] = None
     published_at: Optional[datetime] = None
     post_type_id: Optional[UUID] = None
-    # Image
+    # Media (multi-media support)
+    media_items: List[MediaItem] = Field(default_factory=list)
+    # DEPRECATED: Image (kept for backward compatibility)
     image_url: Optional[str] = None
     # Scheduling fields
     scheduled_at: Optional[datetime] = None
@@ -335,6 +347,11 @@ class GeneratedPost(DBModel):
     # Metadata for additional info (e.g., LinkedIn post URL, auto-posting status)
     metadata: Optional[Dict[str, Any]] = None
 
+    @property
+    def has_media(self) -> bool:
+        """Check if post has any media items."""
+        return len(self.media_items) > 0
+
 
 # ==================== LICENSE KEY MODELS ====================
 

src/services/linkedin_service.py

@@ -35,7 +35,8 @@ class LinkedInService:
         self,
         linkedin_account_id: UUID,
         text: str,
-        image_url: Optional[str] = None
+        image_url: Optional[str] = None,
+        media_items: Optional[list] = None
     ) -> Dict:
         """
         Post content to LinkedIn using UGC Posts API.
@@ -43,7 +44,9 @@ class LinkedInService:
         Args:
             linkedin_account_id: ID of the linkedin_accounts record
             text: Post text content
-            image_url: Optional image URL from Supabase storage
+            image_url: (DEPRECATED) Optional single image URL - use media_items instead
+            media_items: Optional list of media items (dicts with 'type', 'url', 'order')
+                        Supports up to 3 images (carousel) or 1 video
 
         Returns:
             Dict with 'url' key containing the LinkedIn post URL
@@ -80,17 +83,53 @@ class LinkedInService:
             }
         }
 
-        # Handle image upload if provided
+        # Handle media upload (new multi-media support)
-        if image_url:
+        if media_items and len(media_items) > 0:
+            try:
+                media_type = media_items[0].get("type", "image")  # All items have same type
+
+                if media_type == "video":
+                    # Single video upload
+                    video_urn = await self._upload_video(
+                        access_token,
+                        linkedin_user_id,
+                        media_items[0].get("url")
+                    )
+                    if video_urn:
+                        payload["specificContent"]["com.linkedin.ugc.ShareContent"]["shareMediaCategory"] = "VIDEO"
+                        payload["specificContent"]["com.linkedin.ugc.ShareContent"]["media"] = [
+                            {"status": "READY", "media": video_urn}
+                        ]
+
+                elif media_type == "image":
+                    # Upload all images (Carousel if > 1)
+                    media_urns = []
+                    for item in sorted(media_items, key=lambda x: x.get("order", 0)):
+                        urn = await self._upload_image(
+                            access_token,
+                            linkedin_user_id,
+                            item.get("url")
+                        )
+                        if urn:
+                            media_urns.append(urn)
+
+                    if media_urns:
+                        payload["specificContent"]["com.linkedin.ugc.ShareContent"]["shareMediaCategory"] = "IMAGE"
+                        payload["specificContent"]["com.linkedin.ugc.ShareContent"]["media"] = [
+                            {"status": "READY", "media": urn} for urn in media_urns
+                        ]
+
+            except Exception as e:
+                logger.warning(f"Media upload failed for {linkedin_account_id}: {e}. Posting without media.")
+
+        # Backward compatibility: single image_url
+        elif image_url:
             try:
                 media_urn = await self._upload_image(access_token, linkedin_user_id, image_url)
                 if media_urn:
                     payload["specificContent"]["com.linkedin.ugc.ShareContent"]["shareMediaCategory"] = "IMAGE"
                     payload["specificContent"]["com.linkedin.ugc.ShareContent"]["media"] = [
-                        {
+                        {"status": "READY", "media": media_urn}
-                            "status": "READY",
-                            "media": media_urn
-                        }
                     ]
             except Exception as e:
                 logger.warning(f"Image upload failed for {linkedin_account_id}: {e}. Posting without image.")
@@ -213,6 +252,79 @@ class LinkedInService:
             logger.error(f"Image upload error: {e}")
             return None
 
+    async def _upload_video(
+        self,
+        access_token: str,
+        linkedin_user_id: str,
+        video_url: str
+    ) -> Optional[str]:
+        """
+        Upload video to LinkedIn for use in post.
+
+        Returns media URN if successful, None otherwise.
+        """
+        try:
+            # Step 1: Register upload with VIDEO recipe
+            register_payload = {
+                "registerUploadRequest": {
+                    "recipes": ["urn:li:digitalmediaRecipe:feedshare-video"],  # VIDEO recipe
+                    "owner": f"urn:li:person:{linkedin_user_id}",
+                    "serviceRelationships": [
+                        {
+                            "relationshipType": "OWNER",
+                            "identifier": "urn:li:userGeneratedContent"
+                        }
+                    ]
+                }
+            }
+
+            async with httpx.AsyncClient(timeout=60.0) as client:  # Longer timeout for videos
+                register_response = await client.post(
+                    f"{self.BASE_URL}/assets?action=registerUpload",
+                    headers={
+                        "Authorization": f"Bearer {access_token}",
+                        "Content-Type": "application/json"
+                    },
+                    json=register_payload
+                )
+
+                if register_response.status_code != 200:
+                    logger.error(f"Video register failed: {register_response.status_code}")
+                    return None
+
+                register_data = register_response.json()
+                upload_url = register_data["value"]["uploadMechanism"]["com.linkedin.digitalmedia.uploading.MediaUploadHttpRequest"]["uploadUrl"]
+                asset_urn = register_data["value"]["asset"]
+
+                # Step 2: Download video from Supabase
+                video_response = await client.get(video_url)
+                if video_response.status_code != 200:
+                    logger.error(f"Failed to download video from {video_url}")
+                    return None
+
+                video_data = video_response.content
+
+                # Step 3: Upload to LinkedIn
+                upload_response = await client.put(
+                    upload_url,
+                    headers={
+                        "Authorization": f"Bearer {access_token}",
+                        "Content-Type": "application/octet-stream"
+                    },
+                    content=video_data
+                )
+
+                if upload_response.status_code in [200, 201]:
+                    logger.info(f"Video uploaded successfully: {asset_urn}")
+                    return asset_urn
+                else:
+                    logger.error(f"Video upload failed: {upload_response.status_code}")
+                    return None
+
+        except Exception as e:
+            logger.error(f"Video upload error: {e}")
+            return None
+
     async def refresh_access_token(self, linkedin_account_id: UUID) -> bool:
         """
         Attempt to refresh the access token using refresh token.

src/services/scheduler_service.py

@@ -111,11 +111,20 @@ class SchedulerService:
                 # Token refresh failed -> Fall back to email
                 raise Exception("Token expired and refresh failed")
 
-        # Post to LinkedIn
+        # Post to LinkedIn with media items
+        # Convert media_items to dict if needed
+        media_items_list = None
+        if post.media_items:
+            media_items_list = [
+                item.dict() if hasattr(item, 'dict') else item
+                for item in post.media_items
+            ]
+
         result = await linkedin_service.post_to_linkedin(
             linkedin_account_id=linkedin_account.id,
             text=post.post_content,
-            image_url=post.image_url
+            media_items=media_items_list,
+            image_url=post.image_url  # Backward compatibility fallback
         )
 
         # Update post as published with LinkedIn metadata
@@ -178,6 +187,19 @@ class SchedulerService:
 
         display_name = profile.display_name or "dort"
 
+        # Generate media HTML
+        media_html = ""
+        if post.media_items and len(post.media_items) > 0:
+            media_items = [item.dict() if hasattr(item, 'dict') else item for item in post.media_items]
+            for item in sorted(media_items, key=lambda x: x.get('order', 0)):
+                if item.get('type') == 'image':
+                    media_html += f'<img src="{item["url"]}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />'
+                elif item.get('type') == 'video':
+                    media_html += f'<video src="{item["url"]}" controls style="width: 100%; max-height: 400px; border-radius: 8px; margin-top: 15px;"></video>'
+        elif post.image_url:
+            # Backward compatibility
+            media_html = f'<img src="{post.image_url}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />'
+
         html_content = f"""
         <div style="font-family: Arial, sans-serif; max-width: 600px; margin: 0 auto;">
             <h2 style="color: #0a66c2;">Dein LinkedIn Post ist bereit! 🚀</h2>
@@ -191,7 +213,7 @@ class SchedulerService:
                 <div style="background: white; border-radius: 4px; padding: 15px; white-space: pre-wrap; font-size: 14px; line-height: 1.5;">
 {post.post_content[:500]}{'...' if len(post.post_content) > 500 else ''}
                 </div>
-                {f'<img src="{post.image_url}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />' if post.image_url else ''}
+                {media_html}
             </div>
 
             <p><strong>Nächste Schritte:</strong></p>
@@ -229,6 +251,19 @@ class SchedulerService:
         display_name = profile.display_name or "dort"
         linkedin_url = result.get('url', 'https://www.linkedin.com/feed/')
 
+        # Generate media HTML
+        media_html = ""
+        if post.media_items and len(post.media_items) > 0:
+            media_items = [item.dict() if hasattr(item, 'dict') else item for item in post.media_items]
+            for item in sorted(media_items, key=lambda x: x.get('order', 0)):
+                if item.get('type') == 'image':
+                    media_html += f'<img src="{item["url"]}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />'
+                elif item.get('type') == 'video':
+                    media_html += f'<video src="{item["url"]}" controls style="width: 100%; max-height: 400px; border-radius: 8px; margin-top: 15px;"></video>'
+        elif post.image_url:
+            # Backward compatibility
+            media_html = f'<img src="{post.image_url}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />'
+
         html_content = f"""
         <div style="font-family: Arial, sans-serif; max-width: 600px; margin: 0 auto;">
             <h2 style="color: #0a66c2;">Post erfolgreich veröffentlicht! 🎉</h2>
@@ -242,7 +277,7 @@ class SchedulerService:
                 <div style="background: white; border-radius: 4px; padding: 15px; white-space: pre-wrap; font-size: 14px; line-height: 1.5;">
 {post.post_content[:500]}{'...' if len(post.post_content) > 500 else ''}
                 </div>
-                {f'<img src="{post.image_url}" alt="Post-Bild" style="width: 100%; max-height: 400px; object-fit: cover; border-radius: 8px; margin-top: 15px;" />' if post.image_url else ''}
+                {media_html}
             </div>
 
             <p>

src/services/storage_service.py

@@ -7,8 +7,13 @@ from loguru import logger
 from src.config import settings
 
 
-ALLOWED_CONTENT_TYPES = {"image/jpeg", "image/png", "image/gif", "image/webp"}
+ALLOWED_CONTENT_TYPES = {
-MAX_FILE_SIZE = 5 * 1024 * 1024  # 5MB
+    "image/jpeg", "image/png", "image/gif", "image/webp",
+    "video/mp4", "video/webm", "video/quicktime"
+}
+MAX_IMAGE_SIZE = 5 * 1024 * 1024  # 5MB
+MAX_VIDEO_SIZE = 50 * 1024 * 1024  # 50MB
+MAX_FILE_SIZE = MAX_IMAGE_SIZE  # Deprecated: for backward compatibility
 BUCKET_NAME = "post-images"
 
 CONTENT_TYPE_EXTENSIONS = {
@@ -16,6 +21,9 @@ CONTENT_TYPE_EXTENSIONS = {
     "image/png": "png",
     "image/gif": "gif",
     "image/webp": "webp",
+    "video/mp4": "mp4",
+    "video/webm": "webm",
+    "video/quicktime": "mov",
 }
 
 
@@ -49,23 +57,41 @@ class StorageService:
                     raise
         self._bucket_ensured = True
 
-    async def upload_image(
+    async def upload_media(
         self,
         file_content: bytes,
         content_type: str,
         user_id: str,
     ) -> str:
-        """Upload an image to Supabase Storage.
+        """Upload an image or video to Supabase Storage.
 
-        Returns the public URL of the uploaded image.
+        Args:
+            file_content: File bytes
+            content_type: MIME type (e.g., 'image/jpeg', 'video/mp4')
+            user_id: User ID for folder organization
+
+        Returns:
+            Public URL of the uploaded media.
+
+        Raises:
+            ValueError: If content type is not allowed or file is too large.
         """
         if content_type not in ALLOWED_CONTENT_TYPES:
-            raise ValueError(f"Unzulässiger Dateityp: {content_type}. Erlaubt: JPEG, PNG, GIF, WebP")
+            raise ValueError(
+                f"Unzulässiger Dateityp: {content_type}. "
+                f"Erlaubt: JPEG, PNG, GIF, WebP, MP4, WebM, MOV"
+            )
 
-        if len(file_content) > MAX_FILE_SIZE:
+        # Check size based on type
-            raise ValueError(f"Datei zu groß (max. {MAX_FILE_SIZE // 1024 // 1024} MB)")
+        is_video = content_type.startswith("video/")
+        max_size = MAX_VIDEO_SIZE if is_video else MAX_IMAGE_SIZE
 
-        ext = CONTENT_TYPE_EXTENSIONS[content_type]
+        if len(file_content) > max_size:
+            max_mb = max_size // 1024 // 1024
+            media_type = "Video" if is_video else "Bild"
+            raise ValueError(f"{media_type} zu groß (max. {max_mb} MB)")
+
+        ext = CONTENT_TYPE_EXTENSIONS.get(content_type, "bin")
         file_name = f"{user_id}/{uuid.uuid4()}.{ext}"
 
         def _upload():
@@ -79,9 +105,24 @@ class StorageService:
         await asyncio.to_thread(_upload)
 
         public_url = f"{settings.supabase_url}/storage/v1/object/public/{BUCKET_NAME}/{file_name}"
-        logger.info(f"Uploaded image: {file_name}")
+        media_type = "video" if is_video else "image"
+        logger.info(f"Uploaded {media_type}: {file_name}")
         return public_url
 
+    async def upload_image(
+        self,
+        file_content: bytes,
+        content_type: str,
+        user_id: str,
+    ) -> str:
+        """DEPRECATED: Upload an image to Supabase Storage.
+
+        Use upload_media() instead. This method is kept for backward compatibility.
+
+        Returns the public URL of the uploaded image.
+        """
+        return await self.upload_media(file_content, content_type, user_id)
+
     async def delete_image(self, image_url: str) -> None:
         """Delete an image from Supabase Storage by its public URL."""
         prefix = f"{settings.supabase_url}/storage/v1/object/public/{BUCKET_NAME}/"

src/web/templates/user/company_manage_create.html

@@ -232,28 +232,29 @@ oder 'Meine Meinung dazu ist...'"
             <div class="card-bg rounded-xl border p-8">
                 <div id="resultHeader" class="flex items-center justify-between mb-6"></div>
                 <div id="postResult" class="bg-brand-bg/50 rounded-lg p-6 mb-6"></div>
-                <!-- Image Upload Area -->
+                <!-- Media Upload Area (Multi-Media Support) -->
-                <div id="resultImageArea" class="mb-6 hidden">
+                <div id="resultMediaArea" class="mb-6 hidden">
-                    <div id="resultImageUploadZone" class="border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+                    <h4 class="text-white font-semibold mb-3">Medien (<span id="resultMediaCount">0</span>/3)</h4>
-                        <input type="file" id="resultImageInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
+
+                    <!-- Media Grid -->
+                    <div id="resultMediaGrid" class="grid gap-3 mb-3 hidden"></div>
+
+                    <!-- Upload Zone -->
+                    <div id="resultMediaUploadZone" class="border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+                        <input type="file" id="resultMediaInput" accept="image/jpeg,image/png,image/gif,image/webp,video/mp4,video/webm,video/quicktime" class="hidden">
                         <svg class="w-8 h-8 mx-auto mb-2 text-gray-500" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 16l4.586-4.586a2 2 0 012.828 0L16 16m-2-2l1.586-1.586a2 2 0 012.828 0L20 14m-6-6h.01M6 20h12a2 2 0 002-2V6a2 2 0 00-2-2H6a2 2 0 00-2 2v12a2 2 0 002 2z"/></svg>
-                        <p class="text-sm text-gray-400">Bild hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
+                        <p class="text-sm text-gray-400">Bild oder Video hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
-                        <p class="text-xs text-gray-500 mt-1">JPEG, PNG, GIF, WebP - max. 5 MB</p>
+                        <p class="text-xs text-gray-500 mt-1">Bilder: max. 5 MB | Videos: max. 50 MB</p>
+                        <p id="resultMediaTypeWarning" class="text-xs text-yellow-400 mt-2 hidden">⚠️ Kann nicht Bilder und Videos mischen</p>
                     </div>
-                    <div id="resultImageProgress" class="hidden mt-2">
+
+                    <!-- Upload Progress -->
+                    <div id="resultMediaProgress" class="hidden mt-2">
                         <div style="height:4px;background:rgba(61,72,72,0.8);border-radius:2px;overflow:hidden;">
-                            <div id="resultImageProgressBar" style="height:100%;background:#ffc700;border-radius:2px;transition:width 0.3s;width:0%"></div>
+                            <div id="resultMediaProgressBar" style="height:100%;background:#ffc700;border-radius:2px;transition:width 0.3s;width:0%"></div>
                         </div>
                         <p class="text-xs text-gray-400 mt-1 text-center">Wird hochgeladen...</p>
                     </div>
-                    <div id="resultImagePreview" class="hidden mt-3">
-                        <img id="resultImageImg" src="" alt="Post-Bild" class="rounded-lg w-full max-h-64 object-cover mb-2">
-                        <div class="flex gap-2 justify-center">
-                            <button onclick="document.getElementById('resultImageReplaceInput').click()" class="px-3 py-1.5 bg-brand-bg hover:bg-brand-bg-light text-gray-300 rounded-lg text-sm transition-colors">Ersetzen</button>
-                            <button onclick="removeResultImage()" id="removeResultImageBtn" class="px-3 py-1.5 bg-red-600/20 hover:bg-red-600/30 text-red-400 rounded-lg text-sm transition-colors">Entfernen</button>
-                        </div>
-                        <input type="file" id="resultImageReplaceInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
-                    </div>
                 </div>
                 <div id="resultActions" class="flex gap-3 flex-wrap justify-center"></div>
             </div>
@@ -718,12 +719,11 @@ function showFinalResult(result) {
 
     // Store post ID for image upload and show image area
     window.currentResultPostId = result.post_id;
-    const imageArea = document.getElementById('resultImageArea');
+    const mediaArea = document.getElementById('resultMediaArea');
-    imageArea.classList.remove('hidden');
+    mediaArea.classList.remove('hidden');
-    document.getElementById('resultImageUploadZone').classList.remove('hidden');
+    resultMediaItems = []; // Reset media items
-    document.getElementById('resultImagePreview').classList.add('hidden');
+    refreshResultMediaGrid();
-    document.getElementById('resultImageProgress').classList.add('hidden');
+    initResultMediaUpload();
-    initResultImageUpload();
 
     resultActions.innerHTML = `
         <button onclick="copyPost()" class="px-6 py-3 bg-brand-bg hover:bg-brand-bg-light rounded-lg text-white transition-colors flex items-center gap-2">
@@ -871,15 +871,39 @@ function showToast(message, type = 'info') {
 }
 
 // ==================== RESULT IMAGE UPLOAD ====================
-let resultImageInitialized = false;
+// ==================== RESULT MEDIA UPLOAD (Multi-Media) ====================
 
-async function handleResultImageUpload(file) {
+let resultMediaInitialized = false;
+let resultMediaItems = [];
+
+async function handleResultMediaUpload(file) {
     if (!file || !window.currentResultPostId) return;
 
-    const uploadZone = document.getElementById('resultImageUploadZone');
+    const uploadZone = document.getElementById('resultMediaUploadZone');
-    const progressEl = document.getElementById('resultImageProgress');
+    const progressEl = document.getElementById('resultMediaProgress');
-    const progressBar = document.getElementById('resultImageProgressBar');
+    const progressBar = document.getElementById('resultMediaProgressBar');
-    const previewEl = document.getElementById('resultImagePreview');
+    const warningEl = document.getElementById('resultMediaTypeWarning');
+
+    if (resultMediaItems.length >= 3) {
+        showToast('Maximal 3 Medien erlaubt', 'error');
+        return;
+    }
+
+    const isVideo = file.type.startsWith('video/');
+    const hasImages = resultMediaItems.some(item => item.type === 'image');
+    const hasVideos = resultMediaItems.some(item => item.type === 'video');
+
+    if ((isVideo && hasImages) || (!isVideo && hasVideos)) {
+        warningEl.classList.remove('hidden');
+        showToast('Kann nicht Bilder und Videos mischen', 'error');
+        setTimeout(() => warningEl.classList.add('hidden'), 3000);
+        return;
+    }
+
+    if (isVideo && resultMediaItems.length > 0) {
+        showToast('Nur 1 Video pro Post erlaubt', 'error');
+        return;
+    }
 
     uploadZone.classList.add('hidden');
     progressEl.classList.remove('hidden');
@@ -887,10 +911,10 @@ async function handleResultImageUpload(file) {
 
     try {
         const formData = new FormData();
-        formData.append('image', file);
+        formData.append('file', file);
         progressBar.style.width = '60%';
 
-        const response = await fetch(`/api/posts/${window.currentResultPostId}/image`, {
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media`, {
             method: 'POST',
             body: formData
         });
@@ -904,69 +928,216 @@ async function handleResultImageUpload(file) {
 
         const result = await response.json();
         progressBar.style.width = '100%';
-
+        resultMediaItems = result.media_items || [];
-        document.getElementById('resultImageImg').src = result.image_url;
 
         setTimeout(() => {
             progressEl.classList.add('hidden');
-            previewEl.classList.remove('hidden');
+            refreshResultMediaGrid();
         }, 300);
 
-        showToast('Bild erfolgreich hochgeladen!', 'success');
+        const mediaType = isVideo ? 'Video' : 'Bild';
+        showToast(`${mediaType} erfolgreich hochgeladen!`, 'success');
 
     } catch (error) {
-        console.error('Image upload error:', error);
+        console.error('Media upload error:', error);
         showToast('Fehler: ' + error.message, 'error');
         progressEl.classList.add('hidden');
         uploadZone.classList.remove('hidden');
     }
 }
 
-async function removeResultImage() {
+async function deleteResultMedia(index) {
     if (!window.currentResultPostId) return;
-    const btn = document.getElementById('removeResultImageBtn');
+    if (!confirm('Media wirklich löschen?')) return;
-    const originalHTML = btn.innerHTML;
-    btn.innerHTML = 'Wird entfernt...';
-    btn.disabled = true;
 
     try {
-        const response = await fetch(`/api/posts/${window.currentResultPostId}/image`, { method: 'DELETE' });
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media/${index}`, { method: 'DELETE' });
-        if (!response.ok) throw new Error('Löschen fehlgeschlagen');
 
-        document.getElementById('resultImagePreview').classList.add('hidden');
+        if (!response.ok) {
-        document.getElementById('resultImageUploadZone').classList.remove('hidden');
+            const err = await response.json();
-        showToast('Bild entfernt.', 'success');
+            throw new Error(err.detail || 'Löschen fehlgeschlagen');
+        }
+
+        const result = await response.json();
+        resultMediaItems = result.media_items || [];
+
+        refreshResultMediaGrid();
+        showToast('Media entfernt', 'success');
 
     } catch (error) {
-        console.error('Image delete error:', error);
+        console.error('Media delete error:', error);
         showToast('Fehler: ' + error.message, 'error');
-    } finally {
-        btn.innerHTML = originalHTML;
-        btn.disabled = false;
     }
 }
 
-function initResultImageUpload() {
+// Drag-and-drop state for result media
-    if (resultImageInitialized) return;
+let resultDraggedItemData = null;
-    resultImageInitialized = true;
+let resultDraggedArrayIndex = null;
+let resultOriginalDraggedIndex = null;
 
-    const uploadZone = document.getElementById('resultImageUploadZone');
+function refreshResultMediaGrid() {
-    const fileInput = document.getElementById('resultImageInput');
+    const grid = document.getElementById('resultMediaGrid');
-    const replaceInput = document.getElementById('resultImageReplaceInput');
+    const count = document.getElementById('resultMediaCount');
+    const uploadZone = document.getElementById('resultMediaUploadZone');
+
+    count.textContent = resultMediaItems.length;
+
+    if (resultMediaItems.length === 0) {
+        grid.classList.add('hidden');
+        uploadZone.classList.remove('hidden');
+        return;
+    }
+
+    grid.classList.remove('hidden');
+    grid.style.gridTemplateColumns = `repeat(${resultMediaItems.length}, 1fr)`;
+
+    grid.innerHTML = resultMediaItems.map((item, i) => {
+        const isDragged = resultDraggedItemData && item.url === resultDraggedItemData.url;
+        const ghostStyle = isDragged ? 'opacity: 0.3;' : '';
+
+        return `
+        <div class="media-item relative group rounded-lg overflow-hidden"
+             data-array-index="${i}"
+             draggable="true"
+             style="transition: all 0.3s cubic-bezier(0.4, 0, 0.2, 1); ${ghostStyle} cursor: move;">
+            ${item.type === 'image'
+                ? `<img src="${item.url}" alt="Media ${i+1}" class="w-full h-48 object-cover pointer-events-none">`
+                : `<video src="${item.url}" class="w-full h-48 object-cover pointer-events-none" controls></video>`
+            }
+            <button onclick="deleteResultMedia(${item.order})"
+                class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700 z-10">
+                <svg class="w-4 h-4 text-white pointer-events-none" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                    <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                </svg>
+            </button>
+            <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white pointer-events-none">${i+1}</div>
+        </div>
+    `;
+    }).join('');
+
+    if (resultMediaItems.length >= 3) {
+        uploadZone.classList.add('hidden');
+    } else {
+        uploadZone.classList.remove('hidden');
+    }
+
+    // Initialize drag-and-drop for result media
+    initResultMediaDragAndDrop();
+}
+
+function initResultMediaDragAndDrop() {
+    const grid = document.getElementById('resultMediaGrid');
+    if (!grid) return;
+
+    const items = grid.querySelectorAll('.media-item');
+
+    items.forEach(item => {
+        item.addEventListener('dragstart', (e) => {
+            resultDraggedArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+            resultOriginalDraggedIndex = resultDraggedArrayIndex; // Save original position
+            resultDraggedItemData = resultMediaItems[resultDraggedArrayIndex];
+
+            setTimeout(() => {
+                e.currentTarget.style.opacity = '0.3';
+            }, 0);
+
+            e.dataTransfer.effectAllowed = 'move';
+            const rect = e.currentTarget.getBoundingClientRect();
+            e.dataTransfer.setDragImage(e.currentTarget, rect.width / 2, rect.height / 2);
+        });
+
+        item.addEventListener('dragend', async (e) => {
+            e.currentTarget.style.opacity = '1';
+
+            // Save reorder in background only if position changed
+            console.log('🎯 Result dragend:', {resultOriginalDraggedIndex, resultDraggedArrayIndex});
+
+            if (resultOriginalDraggedIndex !== null && resultDraggedArrayIndex !== resultOriginalDraggedIndex) {
+                console.log('💾 Triggering result save...');
+                await saveResultReorderInBackground();
+            } else {
+                console.log('⏭️ Skip result save');
+            }
+
+            resultDraggedItemData = null;
+            resultDraggedArrayIndex = null;
+            resultOriginalDraggedIndex = null;
+        });
+
+        item.addEventListener('dragover', (e) => {
+            e.preventDefault();
+
+            if (resultDraggedArrayIndex === null) return;
+
+            const targetArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+
+            if (targetArrayIndex === resultDraggedArrayIndex) return;
+
+            // INSTANT visual reorder
+            const newMediaItems = [...resultMediaItems];
+            const [movedItem] = newMediaItems.splice(resultDraggedArrayIndex, 1);
+            newMediaItems.splice(targetArrayIndex, 0, movedItem);
+
+            resultMediaItems = newMediaItems;
+            resultDraggedArrayIndex = targetArrayIndex;
+
+            refreshResultMediaGrid();
+        });
+
+        item.addEventListener('drop', (e) => {
+            e.preventDefault();
+        });
+    });
+}
+
+async function saveResultReorderInBackground() {
+    if (!window.currentResultPostId) return;
+
+    try {
+        // Extract original order values from current arrangement
+        const newOrder = resultMediaItems.map(item => item.order);
+
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media/reorder`, {
+            method: 'PUT',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ order: newOrder })
+        });
+
+        if (response.ok) {
+            const result = await response.json();
+            resultMediaItems = result.media_items || [];
+        }
+    } catch (error) {
+        console.error('Background reorder failed:', error);
+    }
+}
+
+function initResultMediaUpload() {
+    if (resultMediaInitialized) return;
+    resultMediaInitialized = true;
+
+    const uploadZone = document.getElementById('resultMediaUploadZone');
+    const fileInput = document.getElementById('resultMediaInput');
 
     if (!uploadZone) return;
 
     uploadZone.addEventListener('click', () => fileInput.click());
-    fileInput.addEventListener('change', (e) => { if (e.target.files[0]) handleResultImageUpload(e.target.files[0]); });
+    fileInput.addEventListener('change', (e) => {
-    if (replaceInput) {
+        if (e.target.files[0]) handleResultMediaUpload(e.target.files[0]);
-        replaceInput.addEventListener('change', (e) => { if (e.target.files[0]) handleResultImageUpload(e.target.files[0]); });
+        e.target.value = '';
-    }
+    });
-    uploadZone.addEventListener('dragover', (e) => { e.preventDefault(); uploadZone.classList.add('border-brand-highlight', 'bg-brand-highlight/5'); });
+
-    uploadZone.addEventListener('dragleave', () => { uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5'); });
+    uploadZone.addEventListener('dragover', (e) => {
+        e.preventDefault();
+        uploadZone.classList.add('border-brand-highlight', 'bg-brand-highlight/5');
+    });
+    uploadZone.addEventListener('dragleave', () => {
+        uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5');
+    });
     uploadZone.addEventListener('drop', (e) => {
         e.preventDefault();
         uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5');
-        if (e.dataTransfer.files[0]) handleResultImageUpload(e.dataTransfer.files[0]);
+        if (e.dataTransfer.files[0]) handleResultMediaUpload(e.dataTransfer.files[0]);
     });
 }
 

src/web/templates/user/company_manage_post_detail.html

@@ -52,6 +52,24 @@
     .image-upload-progress-bar { height: 100%; background: #ffc700; border-radius: 2px; transition: width 0.3s; }
     .loading-spinner { border: 2px solid rgba(255, 199, 0, 0.2); border-top-color: #ffc700; border-radius: 50%; width: 20px; height: 20px; animation: spin 0.8s linear infinite; }
     @keyframes spin { to { transform: rotate(360deg); } }
+    /* Preview Mode Toggle */
+    .preview-mode-btn { padding: 6px 12px; font-size: 12px; font-weight: 500; border-radius: 6px; color: #9ca3af; background: transparent; border: none; cursor: pointer; transition: all 0.2s; display: flex; align-items: center; gap: 6px; }
+    .preview-mode-btn.active { background: rgba(255, 199, 0, 0.2); color: #ffc700; }
+    .preview-mode-btn:hover:not(.active) { color: #d1d5db; }
+    /* Desktop View */
+    .linkedin-preview.desktop-view { max-width: 100%; margin: 0; }
+    /* Mobile View - smartphone mockup */
+    .linkedin-preview.mobile-view { max-width: 375px; margin: 0 auto; border: 12px solid #1f1f1f; border-radius: 36px; box-shadow: 0 20px 60px rgba(0, 0, 0, 0.5), 0 0 0 1px rgba(255, 255, 255, 0.1); position: relative; }
+    .linkedin-preview.mobile-view::before { content: ''; position: absolute; top: -8px; left: 50%; transform: translateX(-50%); width: 60px; height: 4px; background: #2a2a2a; border-radius: 2px; }
+    .linkedin-preview.mobile-view .linkedin-header { padding: 16px; }
+    .linkedin-preview.mobile-view .linkedin-avatar { width: 40px; height: 40px; font-size: 16px; }
+    .linkedin-preview.mobile-view .linkedin-name { font-size: 13px; }
+    .linkedin-preview.mobile-view .linkedin-headline { font-size: 11px; }
+    .linkedin-preview.mobile-view .linkedin-timestamp { font-size: 11px; }
+    .linkedin-preview.mobile-view .linkedin-content { padding: 0 16px 16px; font-size: 13px; line-height: 1.4; }
+    .linkedin-preview.mobile-view .linkedin-engagement { padding: 12px 16px; font-size: 11px; }
+    .linkedin-preview.mobile-view .linkedin-action-btn { font-size: 13px; padding: 14px 8px; gap: 4px; }
+    .linkedin-preview.mobile-view .linkedin-action-btn svg { width: 18px; height: 18px; }
 </style>
 {% endblock %}
 
@@ -106,7 +124,23 @@
             </div>
 
             <!-- LinkedIn Preview -->
-            <div class="linkedin-preview shadow-lg">
+            <div class="mb-4 flex items-center justify-between">
+                <div class="flex items-center gap-2 text-sm text-gray-400">
+                    <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M15 12a3 3 0 11-6 0 3 3 0 016 0z"/><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M2.458 12C3.732 7.943 7.523 5 12 5c4.478 0 8.268 2.943 9.542 7-1.274 4.057-5.064 7-9.542 7-4.477 0-8.268-2.943-9.542-7z"/></svg>
+                    LinkedIn Vorschau
+                </div>
+                <div class="flex items-center gap-1 bg-brand-bg rounded-lg p-1">
+                    <button onclick="setPreviewMode('desktop')" id="desktopPreviewBtn" class="preview-mode-btn active">
+                        <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M9.75 17L9 20l-1 1h8l-1-1-.75-3M3 13h18M5 17h14a2 2 0 002-2V5a2 2 0 00-2-2H5a2 2 0 00-2 2v10a2 2 0 002 2z"/></svg>
+                        Desktop
+                    </button>
+                    <button onclick="setPreviewMode('mobile')" id="mobilePreviewBtn" class="preview-mode-btn">
+                        <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M12 18h.01M8 21h8a2 2 0 002-2V5a2 2 0 00-2-2H8a2 2 0 00-2 2v14a2 2 0 002 2z"/></svg>
+                        Smartphone
+                    </button>
+                </div>
+            </div>
+            <div class="linkedin-preview shadow-lg desktop-view">
                 <div class="linkedin-header">
                     <div class="linkedin-avatar">{{ employee_name[:2] | upper if employee_name else 'UN' }}</div>
                     <div class="linkedin-user-info">
@@ -122,11 +156,25 @@
                     </div>
                 </div>
                 <div class="linkedin-content">{{ post.post_content }}</div>
-                {% if post.image_url %}
+
-                <img id="linkedinPostImage" src="{{ post.image_url }}" alt="Post image" class="linkedin-post-image">
+                <!-- LinkedIn Media Display -->
-                {% else %}
+                <div id="linkedinMediaSection" class="{% if not post.media_items or post.media_items | length == 0 %}{% if not post.image_url %}hidden{% endif %}{% endif %}">
-                <img id="linkedinPostImage" src="" alt="Post image" class="linkedin-post-image" style="display: none;">
+                    {% if post.media_items and post.media_items | length > 0 %}
+                    <div class="grid gap-1" style="grid-template-columns: repeat({{ post.media_items | length if post.media_items | length <= 3 else 3 }}, 1fr);">
+                        {% for item in post.media_items %}
+                        {% if item.type == 'image' %}
+                        <img src="{{ item.url }}" alt="Post media" class="w-full h-48 object-cover">
+                        {% elif item.type == 'video' %}
+                        <video src="{{ item.url }}" class="w-full h-48 object-cover" controls></video>
                         {% endif %}
+                        {% endfor %}
+                    </div>
+                    {% elif post.image_url %}
+                    <!-- Backward compatibility: single image -->
+                    <img src="{{ post.image_url }}" alt="Post image" class="linkedin-post-image">
+                    {% endif %}
+                </div>
+
                 <div class="linkedin-engagement">
                     <svg width="16" height="16" viewBox="0 0 24 24" fill="#0a66c2">
                         <path d="M19.46 11l-3.91-3.91a7 7 0 01-1.69-2.74l-.49-1.47A2.76 2.76 0 0010.76 1 2.75 2.75 0 008 3.74v1.12a9.19 9.19 0 00.46 2.85L8.89 9H4.12A2.12 2.12 0 002 11.12a2.16 2.16 0 00.92 1.76A2.11 2.11 0 002 14.62a2.14 2.14 0 001.28 2 2 2 0 00-.28 1 2.12 2.12 0 002 2.12v.14A2.12 2.12 0 007.12 22h7.49a8.08 8.08 0 003.58-.84l.31-.16H21V11z"/>
@@ -177,40 +225,56 @@
             </div>
         </div>
 
-        <!-- Image Upload -->
+        <!-- Media Upload Section (Multi-Media Support) -->
         <div class="section-card rounded-xl p-6">
             <h3 class="font-semibold text-white mb-4 flex items-center gap-2">
                 <svg class="w-5 h-5 text-brand-highlight" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 16l4.586-4.586a2 2 0 012.828 0L16 16m-2-2l1.586-1.586a2 2 0 012.828 0L20 14m-6-6h.01M6 20h12a2 2 0 002-2V6a2 2 0 00-2-2H6a2 2 0 00-2 2v12a2 2 0 002 2z"/></svg>
-                Bild
+                Medien (<span id="mediaCount">{{ post.media_items | length if post.media_items else 0 }}</span>/3)
             </h3>
-            <div id="imageUploadZone" class="image-upload-zone {% if post.image_url %}hidden{% endif %}">
+
-                <input type="file" id="imageFileInput" accept="image/jpeg,image/png,image/gif,image/webp">
+            <!-- Media Grid (shown when media exists) -->
-                <svg class="w-8 h-8 mx-auto mb-2 text-gray-500" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M7 16a4 4 0 01-.88-7.903A5 5 0 1115.9 6L16 6a5 5 0 011 9.9M15 13l-3-3m0 0l-3 3m3-3v12"/></svg>
+            <div id="mediaGrid" class="grid gap-3 mb-3 {% if not post.media_items or post.media_items | length == 0 %}hidden{% endif %}" style="grid-template-columns: repeat({{ post.media_items | length if post.media_items and post.media_items | length <= 3 else 1 }}, 1fr);">
-                <p class="text-sm text-gray-400">Bild hierher ziehen oder <span class="text-brand-highlight cursor-pointer">durchsuchen</span></p>
+                {% if post.media_items %}
-                <p class="text-xs text-gray-500 mt-1">JPEG, PNG, GIF, WebP - max. 5 MB</p>
+                {% for item in post.media_items %}
+                <div class="media-item relative group rounded-lg overflow-hidden" data-index="{{ item.order if item.order is defined else loop.index0 }}" draggable="true" style="cursor: grab;">
+                    {% if item.type == 'image' %}
+                    <img src="{{ item.url }}" alt="Media {{ loop.index }}" class="w-full h-48 object-cover">
+                    {% elif item.type == 'video' %}
+                    <video src="{{ item.url }}" class="w-full h-48 object-cover" controls></video>
+                    {% endif %}
+
+                    <!-- Delete button -->
+                    <button onclick="deleteMedia({{ item.order if item.order is defined else loop.index0 }})" class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700">
+                        <svg class="w-4 h-4 text-white" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                            <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                        </svg>
+                    </button>
+
+                    <!-- Order badge -->
+                    <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white">
+                        {{ loop.index }}
                     </div>
-            <div id="imageUploadProgress" class="hidden">
+                </div>
+                {% endfor %}
+                {% endif %}
+            </div>
+
+            <!-- Upload Zone (shown when < 3 media items) -->
+            <div id="mediaUploadZone" class="{% if post.media_items and post.media_items | length >= 3 %}hidden{% endif %} border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+                <input type="file" id="mediaFileInput" accept="image/jpeg,image/png,image/gif,image/webp,video/mp4,video/webm,video/quicktime" class="hidden">
+                <svg class="w-8 h-8 mx-auto mb-2 text-gray-500" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M7 16a4 4 0 01-.88-7.903A5 5 0 1115.9 6L16 6a5 5 0 011 9.9M15 13l-3-3m0 0l-3 3m3-3v12"/></svg>
+                <p class="text-sm text-gray-400">Bild oder Video hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
+                <p class="text-xs text-gray-500 mt-1">Bilder: max. 5 MB | Videos: max. 50 MB</p>
+                <p id="mediaTypeWarning" class="text-xs text-yellow-400 mt-2 hidden">⚠️ Kann nicht Bilder und Videos mischen</p>
+            </div>
+
+            <!-- Upload Progress -->
+            <div id="mediaUploadProgress" class="hidden">
                 <div class="image-upload-progress">
-                    <div id="imageProgressBar" class="image-upload-progress-bar" style="width: 0%"></div>
+                    <div id="mediaProgressBar" class="image-upload-progress-bar" style="width: 0%"></div>
                 </div>
                 <p class="text-xs text-gray-400 mt-1 text-center">Wird hochgeladen...</p>
             </div>
-            <div id="imagePreviewSection" class="{% if not post.image_url %}hidden{% endif %}">
-                <div class="image-preview-container mb-3">
-                    <img id="sidebarImagePreview" src="{{ post.image_url or '' }}" alt="Post-Bild">
-                </div>
-                <div class="flex gap-2">
-                    <button onclick="document.getElementById('imageReplaceInput').click()" class="flex-1 px-3 py-2 bg-brand-bg hover:bg-brand-bg-light text-gray-300 rounded-lg transition-colors text-sm flex items-center justify-center gap-2">
-                        <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 4v5h.582m15.356 2A8.001 8.001 0 004.582 9m0 0H9m11 11v-5h-.581m0 0a8.003 8.003 0 01-15.357-2m15.357 2H15"/></svg>
-                        Ersetzen
-                    </button>
-                    <button onclick="removeImage()" id="removeImageBtn" class="flex-1 px-3 py-2 bg-red-600/20 hover:bg-red-600/30 text-red-400 rounded-lg transition-colors text-sm flex items-center justify-center gap-2">
-                        <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M19 7l-.867 12.142A2 2 0 0116.138 21H7.862a2 2 0 01-1.995-1.858L5 7m5 4v6m4-6v6m1-10V4a1 1 0 00-1-1h-4a1 1 0 00-1 1v3M4 7h16"/></svg>
-                        Entfernen
-                    </button>
-                </div>
-                <input type="file" id="imageReplaceInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
-            </div>
         </div>
 
         <!-- Post Info -->
@@ -256,6 +320,25 @@ function copyToClipboard() {
     });
 }
 
+// Preview Mode Toggle (Desktop/Mobile)
+function setPreviewMode(mode) {
+    const preview = document.querySelector('.linkedin-preview');
+    const desktopBtn = document.getElementById('desktopPreviewBtn');
+    const mobileBtn = document.getElementById('mobilePreviewBtn');
+
+    if (mode === 'desktop') {
+        preview.classList.remove('mobile-view');
+        preview.classList.add('desktop-view');
+        desktopBtn.classList.add('active');
+        mobileBtn.classList.remove('active');
+    } else if (mode === 'mobile') {
+        preview.classList.remove('desktop-view');
+        preview.classList.add('mobile-view');
+        mobileBtn.classList.add('active');
+        desktopBtn.classList.remove('active');
+    }
+}
+
 async function updateStatus(newStatus) {
     try {
         const formData = new FormData();
@@ -294,13 +377,38 @@ function showToast(message, type = 'info') {
     }, 3000);
 }
 
-async function handleImageUpload(file) {
+// ==================== MULTI-MEDIA UPLOAD ====================
+
+let currentMediaItems = {{ media_items_dict | tojson | safe }};
+
+async function handleMediaUpload(file) {
     if (!file) return;
 
-    const uploadZone = document.getElementById('imageUploadZone');
+    const uploadZone = document.getElementById('mediaUploadZone');
-    const progressEl = document.getElementById('imageUploadProgress');
+    const progressEl = document.getElementById('mediaUploadProgress');
-    const progressBar = document.getElementById('imageProgressBar');
+    const progressBar = document.getElementById('mediaProgressBar');
-    const previewSection = document.getElementById('imagePreviewSection');
+    const warningEl = document.getElementById('mediaTypeWarning');
+
+    if (currentMediaItems.length >= 3) {
+        showToast('Maximal 3 Medien erlaubt', 'error');
+        return;
+    }
+
+    const isVideo = file.type.startsWith('video/');
+    const hasImages = currentMediaItems.some(item => item.type === 'image');
+    const hasVideos = currentMediaItems.some(item => item.type === 'video');
+
+    if ((isVideo && hasImages) || (!isVideo && hasVideos)) {
+        warningEl.classList.remove('hidden');
+        showToast('Kann nicht Bilder und Videos mischen', 'error');
+        setTimeout(() => warningEl.classList.add('hidden'), 3000);
+        return;
+    }
+
+    if (isVideo && currentMediaItems.length > 0) {
+        showToast('Nur 1 Video pro Post erlaubt', 'error');
+        return;
+    }
 
     uploadZone.classList.add('hidden');
     progressEl.classList.remove('hidden');
@@ -308,10 +416,10 @@ async function handleImageUpload(file) {
 
     try {
         const formData = new FormData();
-        formData.append('image', file);
+        formData.append('file', file);
         progressBar.style.width = '60%';
 
-        const response = await fetch(`/api/posts/${POST_ID}/image`, {
+        const response = await fetch(`/api/posts/${POST_ID}/media`, {
             method: 'POST',
             body: formData
         });
@@ -325,69 +433,265 @@ async function handleImageUpload(file) {
 
         const result = await response.json();
         progressBar.style.width = '100%';
-
+        currentMediaItems = result.media_items || [];
-        document.getElementById('linkedinPostImage').src = result.image_url;
-        document.getElementById('linkedinPostImage').style.display = 'block';
-        document.getElementById('sidebarImagePreview').src = result.image_url;
 
         setTimeout(() => {
             progressEl.classList.add('hidden');
-            previewSection.classList.remove('hidden');
+            refreshMediaGrid();
+            refreshLinkedInPreview();
         }, 300);
 
-        showToast('Bild erfolgreich hochgeladen!', 'success');
+        const mediaType = isVideo ? 'Video' : 'Bild';
+        showToast(`${mediaType} erfolgreich hochgeladen!`, 'success');
 
     } catch (error) {
-        console.error('Image upload error:', error);
+        console.error('Media upload error:', error);
         showToast('Fehler: ' + error.message, 'error');
         progressEl.classList.add('hidden');
         uploadZone.classList.remove('hidden');
     }
 }
 
-async function removeImage() {
+async function deleteMedia(index) {
-    const btn = document.getElementById('removeImageBtn');
+    if (!confirm('Media wirklich löschen?')) return;
-    const originalHTML = btn.innerHTML;
-    btn.innerHTML = '<div class="loading-spinner" style="width:16px;height:16px;"></div>';
-    btn.disabled = true;
 
     try {
-        const response = await fetch(`/api/posts/${POST_ID}/image`, { method: 'DELETE' });
+        const response = await fetch(`/api/posts/${POST_ID}/media/${index}`, { method: 'DELETE' });
-        if (!response.ok) throw new Error('Löschen fehlgeschlagen');
 
-        document.getElementById('linkedinPostImage').style.display = 'none';
+        if (!response.ok) {
-        document.getElementById('imagePreviewSection').classList.add('hidden');
+            const err = await response.json();
-        document.getElementById('imageUploadZone').classList.remove('hidden');
+            throw new Error(err.detail || 'Löschen fehlgeschlagen');
-        showToast('Bild entfernt.', 'success');
+        }
+
+        const result = await response.json();
+        currentMediaItems = result.media_items || [];
+
+        refreshMediaGrid();
+        refreshLinkedInPreview();
+        showToast('Media entfernt', 'success');
 
     } catch (error) {
-        console.error('Image delete error:', error);
+        console.error('Media delete error:', error);
         showToast('Fehler: ' + error.message, 'error');
+    }
+}
+
+function refreshMediaGrid() {
+    const grid = document.getElementById('mediaGrid');
+    const count = document.getElementById('mediaCount');
+    const uploadZone = document.getElementById('mediaUploadZone');
+
+    count.textContent = currentMediaItems.length;
+
+    if (currentMediaItems.length === 0) {
+        grid.classList.add('hidden');
+        uploadZone.classList.remove('hidden');
+        return;
+    }
+
+    grid.classList.remove('hidden');
+    grid.style.gridTemplateColumns = `repeat(${currentMediaItems.length}, 1fr)`;
+
+    grid.innerHTML = currentMediaItems.map((item, i) => {
+        const isDragged = draggedItemData && item.url === draggedItemData.url;
+        const ghostClass = isDragged ? 'is-ghost' : '';
+        const ghostStyle = isDragged ? 'opacity: 0.3;' : '';
+
+        return `
+        <div class="media-item relative group rounded-lg overflow-hidden border-2 border-transparent hover:border-brand-highlight ${ghostClass}"
+             data-array-index="${i}"
+             draggable="true"
+             style="cursor: grab; transition: all 0.3s cubic-bezier(0.4, 0, 0.2, 1); ${ghostStyle}">
+            <div class="media-content">
+                ${item.type === 'image'
+                    ? `<img src="${item.url}" alt="Media ${i+1}" class="w-full h-48 object-cover pointer-events-none">`
+                    : `<video src="${item.url}" class="w-full h-48 object-cover pointer-events-none" controls></video>`
+                }
+            </div>
+            <button onclick="deleteMedia(${item.order})"
+                class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700 z-10">
+                <svg class="w-4 h-4 text-white" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                    <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                </svg>
+            </button>
+            <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white pointer-events-none">${i+1}</div>
+        </div>
+        `;
+    }).join('');
+
+    initDragAndDrop();
+
+    if (currentMediaItems.length >= 3) {
+        uploadZone.classList.add('hidden');
+    } else {
+        uploadZone.classList.remove('hidden');
+    }
+}
+
+function refreshLinkedInPreview() {
+    const linkedinMediaSection = document.getElementById('linkedinMediaSection');
+    if (!linkedinMediaSection) return;
+
+    if (currentMediaItems.length === 0) {
+        linkedinMediaSection.classList.add('hidden');
+        return;
+    }
+
+    linkedinMediaSection.classList.remove('hidden');
+    const gridClass = currentMediaItems.length === 1 ? 'grid-cols-1' :
+                      currentMediaItems.length === 2 ? 'grid-cols-2' : 'grid-cols-3';
+
+    linkedinMediaSection.innerHTML = `
+        <div class="grid ${gridClass} gap-1">
+            ${currentMediaItems.map(item =>
+                item.type === 'image'
+                    ? `<img src="${item.url}" class="w-full h-48 object-cover">`
+                    : `<video src="${item.url}" class="w-full h-48 object-cover" controls></video>`
+            ).join('')}
+        </div>
+    `;
+}
+
+// Drag-and-Drop Reorder (Ultra Smooth with Ghost)
+let draggedArrayIndex = null;
+let originalDraggedIndex = null; // Track the original starting position
+let draggedElement = null;
+let lastTargetIndex = null;
+let isSaving = false;
+let draggedItemData = null;
+
+function initDragAndDrop() {
+    const mediaGrid = document.getElementById('mediaGrid');
+    if (!mediaGrid) return;
+
+    const mediaItems = mediaGrid.querySelectorAll('.media-item');
+
+    mediaItems.forEach((item, idx) => {
+        item.addEventListener('dragstart', (e) => {
+            draggedArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+            originalDraggedIndex = draggedArrayIndex; // Save the original position
+            draggedElement = e.currentTarget;
+            lastTargetIndex = draggedArrayIndex;
+            draggedItemData = currentMediaItems[draggedArrayIndex];
+
+            setTimeout(() => {
+                e.currentTarget.style.opacity = '0.3';
+            }, 0);
+
+            e.dataTransfer.effectAllowed = 'move';
+            e.dataTransfer.setDragImage(e.currentTarget, e.currentTarget.offsetWidth / 2, e.currentTarget.offsetHeight / 2);
+        });
+
+        item.addEventListener('dragend', (e) => {
+            const allItems = mediaGrid.querySelectorAll('.media-item');
+            allItems.forEach(i => {
+                i.style.opacity = '1';
+                i.classList.remove('is-ghost');
+            });
+
+            console.log('🎯 Dragend:', {originalDraggedIndex, lastTargetIndex});
+
+            if (lastTargetIndex !== null && lastTargetIndex !== originalDraggedIndex && !isSaving) {
+                console.log('💾 Triggering save...');
+                saveReorderInBackground();
+            } else {
+                console.log('⏭️ Skip save');
+            }
+
+            draggedArrayIndex = null;
+            originalDraggedIndex = null;
+            draggedElement = null;
+            lastTargetIndex = null;
+            draggedItemData = null;
+        });
+
+        item.addEventListener('dragover', (e) => {
+            e.preventDefault();
+            e.dataTransfer.dropEffect = 'move';
+
+            if (draggedArrayIndex === null) return;
+
+            const targetArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+
+            if (targetArrayIndex !== lastTargetIndex && draggedArrayIndex !== targetArrayIndex) {
+                lastTargetIndex = targetArrayIndex;
+
+                const newMediaItems = [...currentMediaItems];
+                const [movedItem] = newMediaItems.splice(draggedArrayIndex, 1);
+                newMediaItems.splice(targetArrayIndex, 0, movedItem);
+
+                currentMediaItems = newMediaItems;
+                draggedArrayIndex = targetArrayIndex;
+
+                refreshMediaGrid();
+                refreshLinkedInPreview();
+            }
+        });
+
+        item.addEventListener('drop', (e) => {
+            e.preventDefault();
+        });
+    });
+}
+
+async function saveReorderInBackground() {
+    if (isSaving) return;
+    isSaving = true;
+
+    const orderArray = currentMediaItems.map((item, i) => item.order);
+
+    try {
+        const response = await fetch(`/api/posts/${POST_ID}/media/reorder`, {
+            method: 'PUT',
+            headers: {'Content-Type': 'application/json'},
+            body: JSON.stringify({order: orderArray})
+        });
+
+        if (!response.ok) throw new Error('Speichern fehlgeschlagen');
+
+        const result = await response.json();
+        currentMediaItems = result.media_items || [];
+
+        console.log('✓ Reihenfolge im Hintergrund gespeichert');
+
+    } catch (error) {
+        console.error('Background save error:', error);
+        showToast('Fehler beim Speichern - bitte Seite neu laden', 'error');
     } finally {
-        btn.innerHTML = originalHTML;
+        isSaving = false;
-        btn.disabled = false;
     }
 }
 
-document.addEventListener('DOMContentLoaded', () => {
+function initMediaUpload() {
-    const uploadZone = document.getElementById('imageUploadZone');
+    const uploadZone = document.getElementById('mediaUploadZone');
-    const fileInput = document.getElementById('imageFileInput');
+    const fileInput = document.getElementById('mediaFileInput');
-    const replaceInput = document.getElementById('imageReplaceInput');
+
+    if (!uploadZone) return;
 
-    if (uploadZone) {
     uploadZone.addEventListener('click', () => fileInput.click());
-        fileInput.addEventListener('change', (e) => { if (e.target.files[0]) handleImageUpload(e.target.files[0]); });
+    fileInput.addEventListener('change', (e) => {
-        if (replaceInput) {
+        if (e.target.files[0]) handleMediaUpload(e.target.files[0]);
-            replaceInput.addEventListener('change', (e) => { if (e.target.files[0]) handleImageUpload(e.target.files[0]); });
+        e.target.value = '';
-        }
+    });
-        uploadZone.addEventListener('dragover', (e) => { e.preventDefault(); uploadZone.classList.add('dragover'); });
+
-        uploadZone.addEventListener('dragleave', () => { uploadZone.classList.remove('dragover'); });
+    uploadZone.addEventListener('dragover', (e) => {
+        e.preventDefault();
+        uploadZone.classList.add('dragover');
+    });
+    uploadZone.addEventListener('dragleave', () => {
+        uploadZone.classList.remove('dragover');
+    });
     uploadZone.addEventListener('drop', (e) => {
         e.preventDefault();
         uploadZone.classList.remove('dragover');
-            if (e.dataTransfer.files[0]) handleImageUpload(e.dataTransfer.files[0]);
+        if (e.dataTransfer.files[0]) handleMediaUpload(e.dataTransfer.files[0]);
     });
+
+    initDragAndDrop();
 }
+
+document.addEventListener('DOMContentLoaded', () => {
+    initMediaUpload();
 });
 </script>
 {% endblock %}

src/web/templates/user/create_post.html

@@ -227,28 +227,29 @@ oder 'Meine Meinung dazu ist...'"
                 <div id="postResult" class="bg-brand-bg/50 rounded-lg p-6 mb-6">
                     <!-- Final post will be inserted here -->
                 </div>
-                <!-- Image Upload Area -->
+                <!-- Media Upload Area (Multi-Media Support) -->
-                <div id="resultImageArea" class="mb-6 hidden">
+                <div id="resultMediaArea" class="mb-6 hidden">
-                    <div id="resultImageUploadZone" class="border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+                    <h4 class="text-white font-semibold mb-3">Medien (<span id="resultMediaCount">0</span>/3)</h4>
-                        <input type="file" id="resultImageInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
+
+                    <!-- Media Grid -->
+                    <div id="resultMediaGrid" class="grid gap-3 mb-3 hidden"></div>
+
+                    <!-- Upload Zone -->
+                    <div id="resultMediaUploadZone" class="border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+                        <input type="file" id="resultMediaInput" accept="image/jpeg,image/png,image/gif,image/webp,video/mp4,video/webm,video/quicktime" class="hidden">
                         <svg class="w-8 h-8 mx-auto mb-2 text-gray-500" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 16l4.586-4.586a2 2 0 012.828 0L16 16m-2-2l1.586-1.586a2 2 0 012.828 0L20 14m-6-6h.01M6 20h12a2 2 0 002-2V6a2 2 0 00-2-2H6a2 2 0 00-2 2v12a2 2 0 002 2z"/></svg>
-                        <p class="text-sm text-gray-400">Bild hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
+                        <p class="text-sm text-gray-400">Bild oder Video hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
-                        <p class="text-xs text-gray-500 mt-1">JPEG, PNG, GIF, WebP - max. 5 MB</p>
+                        <p class="text-xs text-gray-500 mt-1">Bilder: max. 5 MB | Videos: max. 50 MB</p>
+                        <p id="resultMediaTypeWarning" class="text-xs text-yellow-400 mt-2 hidden">⚠️ Kann nicht Bilder und Videos mischen</p>
                     </div>
-                    <div id="resultImageProgress" class="hidden mt-2">
+
+                    <!-- Upload Progress -->
+                    <div id="resultMediaProgress" class="hidden mt-2">
                         <div style="height:4px;background:rgba(61,72,72,0.8);border-radius:2px;overflow:hidden;">
-                            <div id="resultImageProgressBar" style="height:100%;background:#ffc700;border-radius:2px;transition:width 0.3s;width:0%"></div>
+                            <div id="resultMediaProgressBar" style="height:100%;background:#ffc700;border-radius:2px;transition:width 0.3s;width:0%"></div>
                         </div>
                         <p class="text-xs text-gray-400 mt-1 text-center">Wird hochgeladen...</p>
                     </div>
-                    <div id="resultImagePreview" class="hidden mt-3">
-                        <img id="resultImageImg" src="" alt="Post-Bild" class="rounded-lg w-full max-h-64 object-cover mb-2">
-                        <div class="flex gap-2 justify-center">
-                            <button onclick="document.getElementById('resultImageReplaceInput').click()" class="px-3 py-1.5 bg-brand-bg hover:bg-brand-bg-light text-gray-300 rounded-lg text-sm transition-colors">Ersetzen</button>
-                            <button onclick="removeResultImage()" id="removeResultImageBtn" class="px-3 py-1.5 bg-red-600/20 hover:bg-red-600/30 text-red-400 rounded-lg text-sm transition-colors">Entfernen</button>
-                        </div>
-                        <input type="file" id="resultImageReplaceInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
-                    </div>
                 </div>
                 <div id="resultActions" class="flex gap-3 flex-wrap justify-center">
                     <!-- Action buttons will be inserted here -->
@@ -753,15 +754,14 @@ function showFinalResult(result) {
 
     postResult.innerHTML = `<pre class="whitespace-pre-wrap text-gray-200 font-sans text-lg leading-relaxed">${result.final_post}</pre>`;
 
-    // Store post ID for image upload and show image area
+    // Store post ID for media upload and show media area
     window.currentResultPostId = result.post_id;
-    const imageArea = document.getElementById('resultImageArea');
+    const mediaArea = document.getElementById('resultMediaArea');
-    imageArea.classList.remove('hidden');
+    mediaArea.classList.remove('hidden');
-    // Reset image UI
+    // Reset media UI
-    document.getElementById('resultImageUploadZone').classList.remove('hidden');
+    resultMediaItems = [];
-    document.getElementById('resultImagePreview').classList.add('hidden');
+    refreshResultMediaGrid();
-    document.getElementById('resultImageProgress').classList.add('hidden');
+    initResultMediaUpload();
-    initResultImageUpload();
 
     resultActions.innerHTML = `
         <button onclick="copyPost()" class="px-6 py-3 bg-brand-bg hover:bg-brand-bg-light rounded-lg text-white transition-colors flex items-center gap-2">
@@ -918,15 +918,39 @@ function showToast(message, type = 'info') {
 }
 
 // ==================== RESULT IMAGE UPLOAD ====================
-let resultImageInitialized = false;
+// ==================== RESULT MEDIA UPLOAD (Multi-Media) ====================
 
-async function handleResultImageUpload(file) {
+let resultMediaInitialized = false;
+let resultMediaItems = [];
+
+async function handleResultMediaUpload(file) {
     if (!file || !window.currentResultPostId) return;
 
-    const uploadZone = document.getElementById('resultImageUploadZone');
+    const uploadZone = document.getElementById('resultMediaUploadZone');
-    const progressEl = document.getElementById('resultImageProgress');
+    const progressEl = document.getElementById('resultMediaProgress');
-    const progressBar = document.getElementById('resultImageProgressBar');
+    const progressBar = document.getElementById('resultMediaProgressBar');
-    const previewEl = document.getElementById('resultImagePreview');
+    const warningEl = document.getElementById('resultMediaTypeWarning');
+
+    if (resultMediaItems.length >= 3) {
+        showToast('Maximal 3 Medien erlaubt', 'error');
+        return;
+    }
+
+    const isVideo = file.type.startsWith('video/');
+    const hasImages = resultMediaItems.some(item => item.type === 'image');
+    const hasVideos = resultMediaItems.some(item => item.type === 'video');
+
+    if ((isVideo && hasImages) || (!isVideo && hasVideos)) {
+        warningEl.classList.remove('hidden');
+        showToast('Kann nicht Bilder und Videos mischen', 'error');
+        setTimeout(() => warningEl.classList.add('hidden'), 3000);
+        return;
+    }
+
+    if (isVideo && resultMediaItems.length > 0) {
+        showToast('Nur 1 Video pro Post erlaubt', 'error');
+        return;
+    }
 
     uploadZone.classList.add('hidden');
     progressEl.classList.remove('hidden');
@@ -934,10 +958,10 @@ async function handleResultImageUpload(file) {
 
     try {
         const formData = new FormData();
-        formData.append('image', file);
+        formData.append('file', file);
         progressBar.style.width = '60%';
 
-        const response = await fetch(`/api/posts/${window.currentResultPostId}/image`, {
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media`, {
             method: 'POST',
             body: formData
         });
@@ -951,69 +975,216 @@ async function handleResultImageUpload(file) {
 
         const result = await response.json();
         progressBar.style.width = '100%';
-
+        resultMediaItems = result.media_items || [];
-        document.getElementById('resultImageImg').src = result.image_url;
 
         setTimeout(() => {
             progressEl.classList.add('hidden');
-            previewEl.classList.remove('hidden');
+            refreshResultMediaGrid();
         }, 300);
 
-        showToast('Bild erfolgreich hochgeladen!', 'success');
+        const mediaType = isVideo ? 'Video' : 'Bild';
+        showToast(`${mediaType} erfolgreich hochgeladen!`, 'success');
 
     } catch (error) {
-        console.error('Image upload error:', error);
+        console.error('Media upload error:', error);
         showToast('Fehler: ' + error.message, 'error');
         progressEl.classList.add('hidden');
         uploadZone.classList.remove('hidden');
     }
 }
 
-async function removeResultImage() {
+async function deleteResultMedia(index) {
     if (!window.currentResultPostId) return;
-    const btn = document.getElementById('removeResultImageBtn');
+    if (!confirm('Media wirklich löschen?')) return;
-    const originalHTML = btn.innerHTML;
-    btn.innerHTML = 'Wird entfernt...';
-    btn.disabled = true;
 
     try {
-        const response = await fetch(`/api/posts/${window.currentResultPostId}/image`, { method: 'DELETE' });
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media/${index}`, { method: 'DELETE' });
-        if (!response.ok) throw new Error('Löschen fehlgeschlagen');
 
-        document.getElementById('resultImagePreview').classList.add('hidden');
+        if (!response.ok) {
-        document.getElementById('resultImageUploadZone').classList.remove('hidden');
+            const err = await response.json();
-        showToast('Bild entfernt.', 'success');
+            throw new Error(err.detail || 'Löschen fehlgeschlagen');
+        }
+
+        const result = await response.json();
+        resultMediaItems = result.media_items || [];
+
+        refreshResultMediaGrid();
+        showToast('Media entfernt', 'success');
 
     } catch (error) {
-        console.error('Image delete error:', error);
+        console.error('Media delete error:', error);
         showToast('Fehler: ' + error.message, 'error');
-    } finally {
-        btn.innerHTML = originalHTML;
-        btn.disabled = false;
     }
 }
 
-function initResultImageUpload() {
+// Drag-and-drop state for result media
-    if (resultImageInitialized) return;
+let resultDraggedItemData = null;
-    resultImageInitialized = true;
+let resultDraggedArrayIndex = null;
+let resultOriginalDraggedIndex = null;
 
-    const uploadZone = document.getElementById('resultImageUploadZone');
+function refreshResultMediaGrid() {
-    const fileInput = document.getElementById('resultImageInput');
+    const grid = document.getElementById('resultMediaGrid');
-    const replaceInput = document.getElementById('resultImageReplaceInput');
+    const count = document.getElementById('resultMediaCount');
+    const uploadZone = document.getElementById('resultMediaUploadZone');
+
+    count.textContent = resultMediaItems.length;
+
+    if (resultMediaItems.length === 0) {
+        grid.classList.add('hidden');
+        uploadZone.classList.remove('hidden');
+        return;
+    }
+
+    grid.classList.remove('hidden');
+    grid.style.gridTemplateColumns = `repeat(${resultMediaItems.length}, 1fr)`;
+
+    grid.innerHTML = resultMediaItems.map((item, i) => {
+        const isDragged = resultDraggedItemData && item.url === resultDraggedItemData.url;
+        const ghostStyle = isDragged ? 'opacity: 0.3;' : '';
+
+        return `
+        <div class="media-item relative group rounded-lg overflow-hidden"
+             data-array-index="${i}"
+             draggable="true"
+             style="transition: all 0.3s cubic-bezier(0.4, 0, 0.2, 1); ${ghostStyle} cursor: move;">
+            ${item.type === 'image'
+                ? `<img src="${item.url}" alt="Media ${i+1}" class="w-full h-48 object-cover pointer-events-none">`
+                : `<video src="${item.url}" class="w-full h-48 object-cover pointer-events-none" controls></video>`
+            }
+            <button onclick="deleteResultMedia(${item.order})"
+                class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700 z-10">
+                <svg class="w-4 h-4 text-white pointer-events-none" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                    <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                </svg>
+            </button>
+            <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white pointer-events-none">${i+1}</div>
+        </div>
+    `;
+    }).join('');
+
+    if (resultMediaItems.length >= 3) {
+        uploadZone.classList.add('hidden');
+    } else {
+        uploadZone.classList.remove('hidden');
+    }
+
+    // Initialize drag-and-drop for result media
+    initResultMediaDragAndDrop();
+}
+
+function initResultMediaDragAndDrop() {
+    const grid = document.getElementById('resultMediaGrid');
+    if (!grid) return;
+
+    const items = grid.querySelectorAll('.media-item');
+
+    items.forEach(item => {
+        item.addEventListener('dragstart', (e) => {
+            resultDraggedArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+            resultOriginalDraggedIndex = resultDraggedArrayIndex; // Save original position
+            resultDraggedItemData = resultMediaItems[resultDraggedArrayIndex];
+
+            setTimeout(() => {
+                e.currentTarget.style.opacity = '0.3';
+            }, 0);
+
+            e.dataTransfer.effectAllowed = 'move';
+            const rect = e.currentTarget.getBoundingClientRect();
+            e.dataTransfer.setDragImage(e.currentTarget, rect.width / 2, rect.height / 2);
+        });
+
+        item.addEventListener('dragend', async (e) => {
+            e.currentTarget.style.opacity = '1';
+
+            // Save reorder in background only if position changed
+            console.log('🎯 Result dragend:', {resultOriginalDraggedIndex, resultDraggedArrayIndex});
+
+            if (resultOriginalDraggedIndex !== null && resultDraggedArrayIndex !== resultOriginalDraggedIndex) {
+                console.log('💾 Triggering result save...');
+                await saveResultReorderInBackground();
+            } else {
+                console.log('⏭️ Skip result save');
+            }
+
+            resultDraggedItemData = null;
+            resultDraggedArrayIndex = null;
+            resultOriginalDraggedIndex = null;
+        });
+
+        item.addEventListener('dragover', (e) => {
+            e.preventDefault();
+
+            if (resultDraggedArrayIndex === null) return;
+
+            const targetArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+
+            if (targetArrayIndex === resultDraggedArrayIndex) return;
+
+            // INSTANT visual reorder
+            const newMediaItems = [...resultMediaItems];
+            const [movedItem] = newMediaItems.splice(resultDraggedArrayIndex, 1);
+            newMediaItems.splice(targetArrayIndex, 0, movedItem);
+
+            resultMediaItems = newMediaItems;
+            resultDraggedArrayIndex = targetArrayIndex;
+
+            refreshResultMediaGrid();
+        });
+
+        item.addEventListener('drop', (e) => {
+            e.preventDefault();
+        });
+    });
+}
+
+async function saveResultReorderInBackground() {
+    if (!window.currentResultPostId) return;
+
+    try {
+        // Extract original order values from current arrangement
+        const newOrder = resultMediaItems.map(item => item.order);
+
+        const response = await fetch(`/api/posts/${window.currentResultPostId}/media/reorder`, {
+            method: 'PUT',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ order: newOrder })
+        });
+
+        if (response.ok) {
+            const result = await response.json();
+            resultMediaItems = result.media_items || [];
+        }
+    } catch (error) {
+        console.error('Background reorder failed:', error);
+    }
+}
+
+function initResultMediaUpload() {
+    if (resultMediaInitialized) return;
+    resultMediaInitialized = true;
+
+    const uploadZone = document.getElementById('resultMediaUploadZone');
+    const fileInput = document.getElementById('resultMediaInput');
 
     if (!uploadZone) return;
 
     uploadZone.addEventListener('click', () => fileInput.click());
-    fileInput.addEventListener('change', (e) => { if (e.target.files[0]) handleResultImageUpload(e.target.files[0]); });
+    fileInput.addEventListener('change', (e) => {
-    if (replaceInput) {
+        if (e.target.files[0]) handleResultMediaUpload(e.target.files[0]);
-        replaceInput.addEventListener('change', (e) => { if (e.target.files[0]) handleResultImageUpload(e.target.files[0]); });
+        e.target.value = '';
-    }
+    });
-    uploadZone.addEventListener('dragover', (e) => { e.preventDefault(); uploadZone.classList.add('border-brand-highlight', 'bg-brand-highlight/5'); });
+
-    uploadZone.addEventListener('dragleave', () => { uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5'); });
+    uploadZone.addEventListener('dragover', (e) => {
+        e.preventDefault();
+        uploadZone.classList.add('border-brand-highlight', 'bg-brand-highlight/5');
+    });
+    uploadZone.addEventListener('dragleave', () => {
+        uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5');
+    });
     uploadZone.addEventListener('drop', (e) => {
         e.preventDefault();
         uploadZone.classList.remove('border-brand-highlight', 'bg-brand-highlight/5');
-        if (e.dataTransfer.files[0]) handleResultImageUpload(e.dataTransfer.files[0]);
+        if (e.dataTransfer.files[0]) handleResultMediaUpload(e.dataTransfer.files[0]);
     });
 }
 

src/web/templates/user/post_detail.html

@@ -202,6 +202,92 @@
         background: rgba(255, 199, 0, 0.2);
         color: #ffc700;
     }
+    /* Preview Mode Toggle */
+    .preview-mode-btn {
+        padding: 6px 12px;
+        font-size: 12px;
+        font-weight: 500;
+        border-radius: 6px;
+        color: #9ca3af;
+        background: transparent;
+        border: none;
+        cursor: pointer;
+        transition: all 0.2s;
+        display: flex;
+        align-items: center;
+        gap: 6px;
+    }
+    .preview-mode-btn.active {
+        background: rgba(255, 199, 0, 0.2);
+        color: #ffc700;
+    }
+    .preview-mode-btn:hover:not(.active) {
+        color: #d1d5db;
+    }
+    /* Desktop View - full width */
+    .linkedin-preview.desktop-view {
+        max-width: 100%;
+        margin: 0;
+    }
+    /* Mobile View - smartphone mockup */
+    .linkedin-preview.mobile-view {
+        max-width: 375px;
+        margin: 0 auto;
+        border: 12px solid #1f1f1f;
+        border-radius: 36px;
+        box-shadow: 0 20px 60px rgba(0, 0, 0, 0.5), 0 0 0 1px rgba(255, 255, 255, 0.1);
+        position: relative;
+    }
+    .linkedin-preview.mobile-view::before {
+        content: '';
+        position: absolute;
+        top: -8px;
+        left: 50%;
+        transform: translateX(-50%);
+        width: 60px;
+        height: 4px;
+        background: #2a2a2a;
+        border-radius: 2px;
+    }
+    .linkedin-preview.mobile-view .linkedin-header {
+        padding: 16px;
+    }
+    .linkedin-preview.mobile-view .linkedin-avatar {
+        width: 40px;
+        height: 40px;
+        font-size: 16px;
+    }
+    .linkedin-preview.mobile-view .linkedin-name {
+        font-size: 13px;
+    }
+    .linkedin-preview.mobile-view .linkedin-headline {
+        font-size: 11px;
+    }
+    .linkedin-preview.mobile-view .linkedin-timestamp {
+        font-size: 11px;
+    }
+    .linkedin-preview.mobile-view .linkedin-content {
+        padding: 0 16px 16px;
+        font-size: 13px;
+        line-height: 1.4;
+    }
+    .linkedin-preview.mobile-view .linkedin-see-more {
+        padding: 0 16px 16px;
+        font-size: 13px;
+    }
+    .linkedin-preview.mobile-view .linkedin-engagement {
+        padding: 12px 16px;
+        font-size: 11px;
+    }
+    .linkedin-preview.mobile-view .linkedin-action-btn {
+        font-size: 13px;
+        padding: 14px 8px;
+        gap: 4px;
+    }
+    .linkedin-preview.mobile-view .linkedin-action-btn svg {
+        width: 18px;
+        height: 18px;
+    }
     .view-toggle-btn:hover:not(.active) {
         color: #e5e7eb;
     }
@@ -419,7 +505,23 @@
                 </div>
 
                 <!-- LinkedIn Preview View -->
-                <div id="linkedinPreview" class="linkedin-preview shadow-lg">
+                <div class="mb-4 flex items-center justify-between">
+                    <div class="flex items-center gap-2 text-sm text-gray-400">
+                        <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M15 12a3 3 0 11-6 0 3 3 0 016 0z"/><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M2.458 12C3.732 7.943 7.523 5 12 5c4.478 0 8.268 2.943 9.542 7-1.274 4.057-5.064 7-9.542 7-4.477 0-8.268-2.943-9.542-7z"/></svg>
+                        LinkedIn Vorschau
+                    </div>
+                    <div class="flex items-center gap-1 bg-brand-bg rounded-lg p-1">
+                        <button onclick="setPreviewMode('desktop')" id="desktopPreviewBtn" class="preview-mode-btn active">
+                            <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M9.75 17L9 20l-1 1h8l-1-1-.75-3M3 13h18M5 17h14a2 2 0 002-2V5a2 2 0 00-2-2H5a2 2 0 00-2 2v10a2 2 0 002 2z"/></svg>
+                            Desktop
+                        </button>
+                        <button onclick="setPreviewMode('mobile')" id="mobilePreviewBtn" class="preview-mode-btn">
+                            <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M12 18h.01M8 21h8a2 2 0 002-2V5a2 2 0 00-2-2H8a2 2 0 00-2 2v14a2 2 0 002 2z"/></svg>
+                            Smartphone
+                        </button>
+                    </div>
+                </div>
+                <div id="linkedinPreview" class="linkedin-preview shadow-lg desktop-view">
                     <div class="linkedin-header">
                         <div class="linkedin-avatar">
                             {% if profile_picture_url %}
@@ -447,11 +549,24 @@
                     </div>
                     <div id="linkedinContent" class="linkedin-content collapsed">{{ post.post_content }}</div>
                     <div id="seeMoreBtn" class="linkedin-see-more" onclick="toggleContent()">...mehr anzeigen</div>
-                    {% if post.image_url %}
+
-                    <img id="linkedinPostImage" src="{{ post.image_url }}" alt="Post image" class="linkedin-post-image">
+                    <!-- LinkedIn Media Display -->
-                    {% else %}
+                    <div id="linkedinMediaSection" class="{% if not post.media_items or post.media_items | length == 0 %}{% if not post.image_url %}hidden{% endif %}{% endif %}">
-                    <img id="linkedinPostImage" src="" alt="Post image" class="linkedin-post-image" style="display: none;">
+                        {% if post.media_items and post.media_items | length > 0 %}
+                        <div class="grid gap-1" style="grid-template-columns: repeat({{ post.media_items | length if post.media_items | length <= 3 else 3 }}, 1fr);">
+                            {% for item in post.media_items %}
+                            {% if item.type == 'image' %}
+                            <img src="{{ item.url }}" alt="Post media" class="w-full h-48 object-cover">
+                            {% elif item.type == 'video' %}
+                            <video src="{{ item.url }}" class="w-full h-48 object-cover" controls></video>
                             {% endif %}
+                            {% endfor %}
+                        </div>
+                        {% elif post.image_url %}
+                        <!-- Backward compatibility: single image -->
+                        <img src="{{ post.image_url }}" alt="Post image" class="linkedin-post-image">
+                        {% endif %}
+                    </div>
                     <div class="linkedin-engagement">
                         <svg width="16" height="16" viewBox="0 0 24 24" fill="#0a66c2">
                             <path d="M19.46 11l-3.91-3.91a7 7 0 01-1.69-2.74l-.49-1.47A2.76 2.76 0 0010.76 1 2.75 2.75 0 008 3.74v1.12a9.19 9.19 0 00.46 2.85L8.89 9H4.12A2.12 2.12 0 002 11.12a2.16 2.16 0 00.92 1.76A2.11 2.11 0 002 14.62a2.14 2.14 0 001.28 2 2 2 0 00-.28 1 2.12 2.12 0 002 2.12v.14A2.12 2.12 0 007.12 22h7.49a8.08 8.08 0 003.58-.84l.31-.16H21V11z"/>
@@ -572,46 +687,56 @@
         </div>
     </div>
 
-    <!-- Image Upload Section -->
+    <!-- Media Upload Section (Multi-Media Support) -->
     <div class="section-card rounded-xl p-6 mb-6">
         <h3 class="font-semibold text-white mb-4 flex items-center gap-2">
             <svg class="w-5 h-5 text-brand-highlight" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 16l4.586-4.586a2 2 0 012.828 0L16 16m-2-2l1.586-1.586a2 2 0 012.828 0L20 14m-6-6h.01M6 20h12a2 2 0 002-2V6a2 2 0 00-2-2H6a2 2 0 00-2 2v12a2 2 0 002 2z"/></svg>
-            Bild
+            Medien (<span id="mediaCount">{{ post.media_items | length if post.media_items else 0 }}</span>/3)
         </h3>
 
-        <!-- Upload Zone (shown when no image) -->
+        <!-- Media Grid (shown when media exists) -->
-        <div id="imageUploadZone" class="image-upload-zone {% if post.image_url %}hidden{% endif %}">
+        <div id="mediaGrid" class="grid gap-3 mb-3 {% if not post.media_items or post.media_items | length == 0 %}hidden{% endif %}" style="grid-template-columns: repeat({{ post.media_items | length if post.media_items and post.media_items | length <= 3 else 1 }}, 1fr);">
-            <input type="file" id="imageFileInput" accept="image/jpeg,image/png,image/gif,image/webp">
+            {% if post.media_items %}
+            {% for item in post.media_items %}
+            <div class="media-item relative group rounded-lg overflow-hidden" data-index="{{ item.order if item.order is defined else loop.index0 }}" draggable="true" style="cursor: grab;">
+                {% if item.type == 'image' %}
+                <img src="{{ item.url }}" alt="Media {{ loop.index }}" class="w-full h-48 object-cover">
+                {% elif item.type == 'video' %}
+                <video src="{{ item.url }}" class="w-full h-48 object-cover" controls></video>
+                {% endif %}
+
+                <!-- Delete button -->
+                <button onclick="deleteMedia({{ item.order if item.order is defined else loop.index0 }})" class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700">
+                    <svg class="w-4 h-4 text-white" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                        <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                    </svg>
+                </button>
+
+                <!-- Order badge -->
+                <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white">
+                    {{ loop.index }}
+                </div>
+            </div>
+            {% endfor %}
+            {% endif %}
+        </div>
+
+        <!-- Upload Zone (shown when < 3 media items) -->
+        <div id="mediaUploadZone" class="{% if post.media_items and post.media_items | length >= 3 %}hidden{% endif %} border-2 border-dashed border-brand-bg-light rounded-xl p-6 text-center cursor-pointer hover:border-brand-highlight transition-colors">
+            <input type="file" id="mediaFileInput" accept="image/jpeg,image/png,image/gif,image/webp,video/mp4,video/webm,video/quicktime" class="hidden">
             <svg class="w-8 h-8 mx-auto mb-2 text-gray-500" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M7 16a4 4 0 01-.88-7.903A5 5 0 1115.9 6L16 6a5 5 0 011 9.9M15 13l-3-3m0 0l-3 3m3-3v12"/></svg>
-            <p class="text-sm text-gray-400">Bild hierher ziehen oder <span class="text-brand-highlight cursor-pointer">durchsuchen</span></p>
+            <p class="text-sm text-gray-400">Bild oder Video hierher ziehen oder <span class="text-brand-highlight">durchsuchen</span></p>
-            <p class="text-xs text-gray-500 mt-1">JPEG, PNG, GIF, WebP - max. 5 MB</p>
+            <p class="text-xs text-gray-500 mt-1">Bilder: max. 5 MB | Videos: max. 50 MB</p>
+            <p id="mediaTypeWarning" class="text-xs text-yellow-400 mt-2 hidden">⚠️ Kann nicht Bilder und Videos mischen</p>
         </div>
 
         <!-- Upload Progress -->
-        <div id="imageUploadProgress" class="hidden">
+        <div id="mediaUploadProgress" class="hidden">
             <div class="image-upload-progress">
-                <div id="imageProgressBar" class="image-upload-progress-bar" style="width: 0%"></div>
+                <div id="mediaProgressBar" class="image-upload-progress-bar" style="width: 0%"></div>
             </div>
             <p class="text-xs text-gray-400 mt-1 text-center">Wird hochgeladen...</p>
         </div>
-
-        <!-- Image Preview (shown when image exists) -->
-        <div id="imagePreviewSection" class="{% if not post.image_url %}hidden{% endif %}">
-            <div class="image-preview-container mb-3">
-                <img id="sidebarImagePreview" src="{{ post.image_url or '' }}" alt="Post-Bild">
-            </div>
-            <div class="flex gap-2">
-                <button onclick="document.getElementById('imageReplaceInput').click()" class="flex-1 px-3 py-2 bg-brand-bg hover:bg-brand-bg-light text-gray-300 rounded-lg transition-colors text-sm flex items-center justify-center gap-2">
-                    <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 4v5h.582m15.356 2A8.001 8.001 0 004.582 9m0 0H9m11 11v-5h-.581m0 0a8.003 8.003 0 01-15.357-2m15.357 2H15"/></svg>
-                    Ersetzen
-                </button>
-                <button onclick="removeImage()" id="removeImageBtn" class="flex-1 px-3 py-2 bg-red-600/20 hover:bg-red-600/30 text-red-400 rounded-lg transition-colors text-sm flex items-center justify-center gap-2">
-                    <svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M19 7l-.867 12.142A2 2 0 0116.138 21H7.862a2 2 0 01-1.995-1.858L5 7m5 4v6m4-6v6m1-10V4a1 1 0 00-1-1h-4a1 1 0 00-1 1v3M4 7h16"/></svg>
-                    Entfernen
-                </button>
-            </div>
-            <input type="file" id="imageReplaceInput" accept="image/jpeg,image/png,image/gif,image/webp" class="hidden">
-        </div>
     </div>
 
     <!-- Bottom Section: Score, Feedback, Actions -->
@@ -884,6 +1009,25 @@ function setView(view) {
     }
 }
 
+// Preview Mode Toggle (Desktop/Mobile)
+function setPreviewMode(mode) {
+    const preview = document.getElementById('linkedinPreview');
+    const desktopBtn = document.getElementById('desktopPreviewBtn');
+    const mobileBtn = document.getElementById('mobilePreviewBtn');
+
+    if (mode === 'desktop') {
+        preview.classList.remove('mobile-view');
+        preview.classList.add('desktop-view');
+        desktopBtn.classList.add('active');
+        mobileBtn.classList.remove('active');
+    } else if (mode === 'mobile') {
+        preview.classList.remove('desktop-view');
+        preview.classList.add('mobile-view');
+        mobileBtn.classList.add('active');
+        desktopBtn.classList.remove('active');
+    }
+}
+
 // Edit functions
 function updateCharCount() {
     const textarea = document.getElementById('editTextarea');
@@ -1289,15 +1433,41 @@ function changeVersion(delta) {
     document.getElementById('nextVersion').disabled = currentVersion === totalVersions - 1;
 }
 
-// ==================== IMAGE UPLOAD ====================
+// ==================== MULTI-MEDIA UPLOAD ====================
 
-async function handleImageUpload(file) {
+let currentMediaItems = {{ media_items_dict | tojson | safe }};
+
+async function handleMediaUpload(file) {
     if (!file) return;
 
-    const uploadZone = document.getElementById('imageUploadZone');
+    const uploadZone = document.getElementById('mediaUploadZone');
-    const progressEl = document.getElementById('imageUploadProgress');
+    const progressEl = document.getElementById('mediaUploadProgress');
-    const progressBar = document.getElementById('imageProgressBar');
+    const progressBar = document.getElementById('mediaProgressBar');
-    const previewSection = document.getElementById('imagePreviewSection');
+    const warningEl = document.getElementById('mediaTypeWarning');
+
+    // Validate max 3
+    if (currentMediaItems.length >= 3) {
+        showToast('Maximal 3 Medien erlaubt', 'error');
+        return;
+    }
+
+    // Validate no mixing
+    const isVideo = file.type.startsWith('video/');
+    const hasImages = currentMediaItems.some(item => item.type === 'image');
+    const hasVideos = currentMediaItems.some(item => item.type === 'video');
+
+    if ((isVideo && hasImages) || (!isVideo && hasVideos)) {
+        warningEl.classList.remove('hidden');
+        showToast('Kann nicht Bilder und Videos mischen', 'error');
+        setTimeout(() => warningEl.classList.add('hidden'), 3000);
+        return;
+    }
+
+    // Only 1 video allowed
+    if (isVideo && currentMediaItems.length > 0) {
+        showToast('Nur 1 Video pro Post erlaubt', 'error');
+        return;
+    }
 
     // Show progress
     uploadZone.classList.add('hidden');
@@ -1306,11 +1476,11 @@ async function handleImageUpload(file) {
 
     try {
         const formData = new FormData();
-        formData.append('image', file);
+        formData.append('file', file);
 
         progressBar.style.width = '60%';
 
-        const response = await fetch(`/api/posts/${postId}/image`, {
+        const response = await fetch(`/api/posts/${postId}/media`, {
             method: 'POST',
             body: formData
         });
@@ -1325,64 +1495,319 @@ async function handleImageUpload(file) {
         const result = await response.json();
         progressBar.style.width = '100%';
 
-        // Update UI
+        // Update current media items
-        const linkedinImg = document.getElementById('linkedinPostImage');
+        currentMediaItems = result.media_items || [];
-        const sidebarImg = document.getElementById('sidebarImagePreview');
-
-        linkedinImg.src = result.image_url;
-        linkedinImg.style.display = 'block';
-        sidebarImg.src = result.image_url;
 
         setTimeout(() => {
             progressEl.classList.add('hidden');
-            previewSection.classList.remove('hidden');
+            refreshMediaGrid();
+            refreshLinkedInPreview();
         }, 300);
 
-        showToast('Bild erfolgreich hochgeladen!', 'success');
+        const mediaType = isVideo ? 'Video' : 'Bild';
+        showToast(`${mediaType} erfolgreich hochgeladen!`, 'success');
 
     } catch (error) {
-        console.error('Image upload error:', error);
+        console.error('Media upload error:', error);
         showToast('Fehler: ' + error.message, 'error');
         progressEl.classList.add('hidden');
         uploadZone.classList.remove('hidden');
     }
 }
 
-async function removeImage() {
+async function deleteMedia(index) {
-    const btn = document.getElementById('removeImageBtn');
+    if (!confirm('Media wirklich löschen?')) return;
-    const originalHTML = btn.innerHTML;
-    btn.innerHTML = '<div class="loading-spinner" style="width:16px;height:16px;"></div>';
-    btn.disabled = true;
 
     try {
-        const response = await fetch(`/api/posts/${postId}/image`, {
+        const response = await fetch(`/api/posts/${postId}/media/${index}`, {
             method: 'DELETE'
         });
 
         if (!response.ok) {
-            throw new Error('Löschen fehlgeschlagen');
+            const err = await response.json();
+            throw new Error(err.detail || 'Löschen fehlgeschlagen');
         }
 
-        // Update UI
+        const result = await response.json();
-        document.getElementById('linkedinPostImage').style.display = 'none';
+        currentMediaItems = result.media_items || [];
-        document.getElementById('imagePreviewSection').classList.add('hidden');
-        document.getElementById('imageUploadZone').classList.remove('hidden');
 
-        showToast('Bild entfernt.', 'success');
+        refreshMediaGrid();
+        refreshLinkedInPreview();
+        showToast('Media entfernt', 'success');
 
     } catch (error) {
-        console.error('Image delete error:', error);
+        console.error('Media delete error:', error);
         showToast('Fehler: ' + error.message, 'error');
-    } finally {
-        btn.innerHTML = originalHTML;
-        btn.disabled = false;
     }
 }
 
-function initImageUpload() {
+function refreshMediaGrid() {
-    const uploadZone = document.getElementById('imageUploadZone');
+    const grid = document.getElementById('mediaGrid');
-    const fileInput = document.getElementById('imageFileInput');
+    const count = document.getElementById('mediaCount');
-    const replaceInput = document.getElementById('imageReplaceInput');
+    const uploadZone = document.getElementById('mediaUploadZone');
+
+    count.textContent = currentMediaItems.length;
+
+    if (currentMediaItems.length === 0) {
+        grid.classList.add('hidden');
+        uploadZone.classList.remove('hidden');
+        return;
+    }
+
+    grid.classList.remove('hidden');
+    grid.style.gridTemplateColumns = `repeat(${currentMediaItems.length}, 1fr)`;
+
+    grid.innerHTML = currentMediaItems.map((item, i) => `
+        <div class="media-item relative group rounded-lg overflow-hidden border-2 border-transparent hover:border-brand-highlight"
+             data-array-index="${i}"
+             draggable="true"
+             style="cursor: grab; transition: all 0.3s cubic-bezier(0.4, 0, 0.2, 1);">
+            <div class="media-content">
+                ${item.type === 'image'
+                    ? `<img src="${item.url}" alt="Media ${i+1}" class="w-full h-48 object-cover pointer-events-none">`
+                    : `<video src="${item.url}" class="w-full h-48 object-cover pointer-events-none" controls></video>`
+                }
+            </div>
+            <button onclick="deleteMedia(${item.order})"
+                class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700 z-10">
+                <svg class="w-4 h-4 text-white" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                    <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                </svg>
+            </button>
+            <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white pointer-events-none">${i+1}</div>
+        </div>
+    `).join('');
+
+    // Re-attach drag handlers after refresh
+    initDragAndDrop();
+
+    if (currentMediaItems.length >= 3) {
+        uploadZone.classList.add('hidden');
+    } else {
+        uploadZone.classList.remove('hidden');
+    }
+}
+
+function refreshLinkedInPreview() {
+    const linkedinMediaSection = document.getElementById('linkedinMediaSection');
+
+    if (!linkedinMediaSection) return;
+
+    if (currentMediaItems.length === 0) {
+        linkedinMediaSection.classList.add('hidden');
+        return;
+    }
+
+    linkedinMediaSection.classList.remove('hidden');
+
+    const gridClass = currentMediaItems.length === 1 ? 'grid-cols-1' :
+                      currentMediaItems.length === 2 ? 'grid-cols-2' : 'grid-cols-3';
+
+    linkedinMediaSection.innerHTML = `
+        <div class="grid ${gridClass} gap-1">
+            ${currentMediaItems.map(item =>
+                item.type === 'image'
+                    ? `<img src="${item.url}" class="w-full h-48 object-cover">`
+                    : `<video src="${item.url}" class="w-full h-48 object-cover" controls></video>`
+            ).join('')}
+        </div>
+    `;
+}
+
+// Drag-and-Drop Reorder (Ultra Smooth with Ghost)
+let draggedArrayIndex = null;
+let originalDraggedIndex = null; // Track the original starting position
+let draggedElement = null;
+let lastTargetIndex = null;
+let isSaving = false;
+let draggedItemData = null;
+
+function initDragAndDrop() {
+    const mediaGrid = document.getElementById('mediaGrid');
+    if (!mediaGrid) return;
+
+    const mediaItems = mediaGrid.querySelectorAll('.media-item');
+
+    mediaItems.forEach((item, idx) => {
+        // Dragstart - Element wird gegriffen
+        item.addEventListener('dragstart', (e) => {
+            draggedArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+            originalDraggedIndex = draggedArrayIndex; // Save the original position
+            draggedElement = e.currentTarget;
+            lastTargetIndex = draggedArrayIndex;
+            draggedItemData = currentMediaItems[draggedArrayIndex];
+
+            // Smooth fade out des gezogenen Elements
+            setTimeout(() => {
+                e.currentTarget.style.opacity = '0.3';
+            }, 0);
+
+            e.dataTransfer.effectAllowed = 'move';
+            e.dataTransfer.setDragImage(e.currentTarget, e.currentTarget.offsetWidth / 2, e.currentTarget.offsetHeight / 2);
+        });
+
+        // Dragend - Element wird losgelassen
+        item.addEventListener('dragend', (e) => {
+            // Entferne alle Ghost-Klassen
+            const allItems = mediaGrid.querySelectorAll('.media-item');
+            allItems.forEach(i => {
+                i.style.opacity = '1';
+                i.classList.remove('is-ghost');
+            });
+
+            // Wenn sich die Position geändert hat, speichere im Hintergrund
+            console.log('🎯 Dragend:', {originalDraggedIndex, lastTargetIndex, changed: lastTargetIndex !== null && lastTargetIndex !== originalDraggedIndex});
+
+            if (lastTargetIndex !== null && lastTargetIndex !== originalDraggedIndex && !isSaving) {
+                console.log('💾 Triggering save...');
+                saveReorderInBackground();
+            } else {
+                console.log('⏭️ Skip save:', {lastTargetIndex, originalDraggedIndex, isSaving});
+            }
+
+            draggedArrayIndex = null;
+            originalDraggedIndex = null;
+            draggedElement = null;
+            lastTargetIndex = null;
+            draggedItemData = null;
+        });
+
+        // Dragover - Element schwebt über anderem Element (LIVE REORDER)
+        item.addEventListener('dragover', (e) => {
+            e.preventDefault();
+            e.dataTransfer.dropEffect = 'move';
+
+            if (draggedArrayIndex === null) return;
+
+            const targetArrayIndex = parseInt(e.currentTarget.dataset.arrayIndex);
+
+            // Nur neu ordnen wenn sich die Position geändert hat
+            if (targetArrayIndex !== lastTargetIndex && draggedArrayIndex !== targetArrayIndex) {
+                lastTargetIndex = targetArrayIndex;
+
+                // SOFORTIGES visuelles Update
+                const newMediaItems = [...currentMediaItems];
+                const [movedItem] = newMediaItems.splice(draggedArrayIndex, 1);
+                newMediaItems.splice(targetArrayIndex, 0, movedItem);
+
+                currentMediaItems = newMediaItems;
+                draggedArrayIndex = targetArrayIndex;
+
+                // Smooth Re-Render
+                refreshMediaGridSmooth();
+                refreshLinkedInPreview();
+            }
+        });
+
+        // Drop - Element wird losgelassen
+        item.addEventListener('drop', (e) => {
+            e.preventDefault();
+        });
+    });
+}
+
+// Smooth version of refreshMediaGrid that maintains the dragging state
+function refreshMediaGridSmooth() {
+    const grid = document.getElementById('mediaGrid');
+    const count = document.getElementById('mediaCount');
+    const uploadZone = document.getElementById('mediaUploadZone');
+
+    count.textContent = currentMediaItems.length;
+
+    if (currentMediaItems.length === 0) {
+        grid.classList.add('hidden');
+        uploadZone.classList.remove('hidden');
+        return;
+    }
+
+    grid.classList.remove('hidden');
+    grid.style.gridTemplateColumns = `repeat(${currentMediaItems.length}, 1fr)`;
+
+    grid.innerHTML = currentMediaItems.map((item, i) => {
+        const isDragged = draggedItemData && item.url === draggedItemData.url;
+        const ghostClass = isDragged ? 'is-ghost' : '';
+        const ghostStyle = isDragged ? 'opacity: 0.3;' : '';
+
+        return `
+        <div class="media-item relative group rounded-lg overflow-hidden border-2 border-transparent hover:border-brand-highlight ${ghostClass}"
+             data-array-index="${i}"
+             draggable="true"
+             style="cursor: grab; transition: all 0.3s cubic-bezier(0.4, 0, 0.2, 1); ${ghostStyle}">
+            <div class="media-content">
+                ${item.type === 'image'
+                    ? `<img src="${item.url}" alt="Media ${i+1}" class="w-full h-48 object-cover pointer-events-none">`
+                    : `<video src="${item.url}" class="w-full h-48 object-cover pointer-events-none" controls></video>`
+                }
+            </div>
+            <button onclick="deleteMedia(${item.order})"
+                class="absolute top-2 right-2 p-2 bg-red-600 rounded-full opacity-0 group-hover:opacity-100 transition-opacity hover:bg-red-700 z-10">
+                <svg class="w-4 h-4 text-white" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+                    <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M6 18L18 6M6 6l12 12"/>
+                </svg>
+            </button>
+            <div class="absolute bottom-2 left-2 px-2 py-1 bg-black/50 rounded text-xs text-white pointer-events-none">${i+1}</div>
+        </div>
+        `;
+    }).join('');
+
+    if (currentMediaItems.length >= 3) {
+        uploadZone.classList.add('hidden');
+    } else {
+        uploadZone.classList.remove('hidden');
+    }
+
+    // Re-attach drag handlers
+    initDragAndDrop();
+}
+
+// Speichert die neue Reihenfolge im Hintergrund
+async function saveReorderInBackground() {
+    if (isSaving) return;
+    isSaving = true;
+
+    // Erstelle Order-Array für Backend
+    const orderArray = currentMediaItems.map((item, i) => item.order);
+
+    console.log('🔍 Sending reorder:', {
+        currentMediaItems: currentMediaItems.map(item => ({url: item.url.substring(item.url.length-20), order: item.order})),
+        orderArray: orderArray
+    });
+
+    try {
+        const response = await fetch(`/api/posts/${postId}/media/reorder`, {
+            method: 'PUT',
+            headers: {'Content-Type': 'application/json'},
+            body: JSON.stringify({order: orderArray})
+        });
+
+        if (!response.ok) {
+            const errorData = await response.json().catch(() => ({}));
+            console.error('❌ Reorder failed:', response.status, errorData);
+            throw new Error('Speichern fehlgeschlagen: ' + (errorData.detail || response.statusText));
+        }
+
+        const result = await response.json();
+        console.log('✅ Reorder response:', {
+            received: result.media_items.map(item => ({url: item.url.substring(item.url.length-20), order: item.order}))
+        });
+
+        // Update mit Server-Response (für korrekte order-Werte)
+        currentMediaItems = result.media_items || [];
+
+        // Stilles Update ohne Re-Render (UI ist schon aktuell)
+        console.log('✓ Reihenfolge im Hintergrund gespeichert');
+
+    } catch (error) {
+        console.error('Background save error:', error);
+        showToast('Fehler beim Speichern - bitte Seite neu laden', 'error');
+    } finally {
+        isSaving = false;
+    }
+}
+
+function initMediaUpload() {
+    const uploadZone = document.getElementById('mediaUploadZone');
+    const fileInput = document.getElementById('mediaFileInput');
 
     if (!uploadZone) return;
 
@@ -1391,17 +1816,11 @@ function initImageUpload() {
 
     // File selected
     fileInput.addEventListener('change', (e) => {
-        if (e.target.files[0]) handleImageUpload(e.target.files[0]);
+        if (e.target.files[0]) handleMediaUpload(e.target.files[0]);
+        e.target.value = ''; // Reset input
     });
 
-    // Replace input
+    // Drag & drop for upload zone
-    if (replaceInput) {
-        replaceInput.addEventListener('change', (e) => {
-            if (e.target.files[0]) handleImageUpload(e.target.files[0]);
-        });
-    }
-
-    // Drag & drop
     uploadZone.addEventListener('dragover', (e) => {
         e.preventDefault();
         uploadZone.classList.add('dragover');
@@ -1412,8 +1831,11 @@ function initImageUpload() {
     uploadZone.addEventListener('drop', (e) => {
         e.preventDefault();
         uploadZone.classList.remove('dragover');
-        if (e.dataTransfer.files[0]) handleImageUpload(e.dataTransfer.files[0]);
+        if (e.dataTransfer.files[0]) handleMediaUpload(e.dataTransfer.files[0]);
     });
+
+    // Initialize drag-and-drop for reordering
+    initDragAndDrop();
 }
 
 // Initialize
@@ -1430,8 +1852,8 @@ document.addEventListener('DOMContentLoaded', () => {
     // Initialize LinkedIn preview
     initLinkedInPreview();
 
-    // Initialize image upload
+    // Initialize media upload (multi-media support)
-    initImageUpload();
+    initMediaUpload();
 
     // Add event listener for textarea character count
     const textarea = document.getElementById('editTextarea');

src/web/user/routes.py

@@ -1533,6 +1533,14 @@ async def post_detail_page(request: Request, post_id: str):
         if post.critic_feedback and len(post.critic_feedback) > 0:
             final_feedback = post.critic_feedback[-1]
 
+        # Convert media_items to dicts for JSON serialization in template
+        media_items_dict = []
+        if post.media_items:
+            media_items_dict = [
+                item.model_dump(mode='json') if hasattr(item, 'model_dump') else (item.dict() if hasattr(item, 'dict') else item)
+                for item in post.media_items
+            ]
+
         return templates.TemplateResponse("post_detail.html", {
             "request": request,
             "page": "posts",
@@ -1544,7 +1552,8 @@ async def post_detail_page(request: Request, post_id: str):
             "post_type": post_type,
             "post_type_analysis": post_type_analysis,
             "final_feedback": final_feedback,
-            "profile_picture_url": profile_picture_url
+            "profile_picture_url": profile_picture_url,
+            "media_items_dict": media_items_dict
         })
     except Exception as e:
         logger.error(f"Error loading post detail: {e}")
@@ -2679,6 +2688,14 @@ async def company_manage_post_detail(request: Request, post_id: str, employee_id
 
     profile = await db.get_profile(emp_profile.id)
 
+    # Convert media_items to dicts for JSON serialization in template
+    media_items_dict = []
+    if post.media_items:
+        media_items_dict = [
+            item.model_dump(mode='json') if hasattr(item, 'model_dump') else (item.dict() if hasattr(item, 'dict') else item)
+            for item in post.media_items
+        ]
+
     return templates.TemplateResponse("company_manage_post_detail.html", {
         "request": request,
         "page": "manage",
@@ -2686,7 +2703,8 @@ async def company_manage_post_detail(request: Request, post_id: str, employee_id
         "employee_id": employee_id,
         "employee_name": emp_user.linkedin_name or emp_profile.display_name or emp_user.email,
         "profile": profile,
-        "post": post
+        "post": post,
+        "media_items_dict": media_items_dict
     })
 
 
@@ -3433,61 +3451,18 @@ async def unschedule_post(request: Request, post_id: str):
 
 @user_router.post("/api/posts/{post_id}/image")
 async def upload_post_image(request: Request, post_id: str):
-    """Upload or replace an image for a post."""
+    """DEPRECATED: Upload or replace an image for a post.
-    session = require_user_session(request)
-    if not session:
-        raise HTTPException(status_code=401, detail="Not authenticated")
 
-    try:
+    Use /api/posts/{post_id}/media instead. This endpoint is kept for backward compatibility.
-        post = await db.get_generated_post(UUID(post_id))
+    """
-        if not post:
+    # Delegate to new media upload endpoint
-            raise HTTPException(status_code=404, detail="Post not found")
+    result = await upload_post_media(request, post_id)
 
-        # Check authorization: owner or company owner
+    # Return legacy format for compatibility
-        is_owner = session.user_id and str(post.user_id) == session.user_id
+    if result.get("success") and result.get("media_item"):
-        is_company_owner = False
+        return {"success": True, "image_url": result["media_item"]["url"]}
-        if not is_owner and session.account_type == "company" and session.company_id:
-            profile = await db.get_profile(post.user_id)
-            if profile and profile.company_id and str(profile.company_id) == session.company_id:
-                is_company_owner = True
-        if not is_owner and not is_company_owner:
-            raise HTTPException(status_code=403, detail="Not authorized")
 
-        # Read file from form data
+    return result
-        form = await request.form()
-        image = form.get("image")
-        if not image or not hasattr(image, "read"):
-            raise HTTPException(status_code=400, detail="No image file provided")
-
-        file_content = await image.read()
-        content_type = image.content_type or "application/octet-stream"
-
-        # Delete old image if exists
-        if post.image_url:
-            try:
-                await storage.delete_image(post.image_url)
-            except Exception as e:
-                logger.warning(f"Failed to delete old image: {e}")
-
-        # Upload new image
-        image_url = await storage.upload_image(
-            file_content=file_content,
-            content_type=content_type,
-            user_id=str(post.user_id),
-        )
-
-        # Update post record
-        await db.update_generated_post(UUID(post_id), {"image_url": image_url})
-
-        return {"success": True, "image_url": image_url}
-
-    except HTTPException:
-        raise
-    except ValueError as e:
-        raise HTTPException(status_code=400, detail=str(e))
-    except Exception as e:
-        logger.exception(f"Failed to upload post image: {e}")
-        raise HTTPException(status_code=500, detail=str(e))
 
 
 @user_router.delete("/api/posts/{post_id}/image")
@@ -3531,6 +3506,209 @@ async def delete_post_image(request: Request, post_id: str):
         raise HTTPException(status_code=500, detail=str(e))
 
 
+# ==================== POST MEDIA UPLOAD (MULTI-MEDIA) ====================
+
+@user_router.post("/api/posts/{post_id}/media")
+async def upload_post_media(request: Request, post_id: str):
+    """Upload a media item (image or video). Max 3 items per post."""
+    session = require_user_session(request)
+    if not session:
+        raise HTTPException(status_code=401, detail="Not authenticated")
+
+    try:
+        post = await db.get_generated_post(UUID(post_id))
+        if not post:
+            raise HTTPException(status_code=404, detail="Post not found")
+
+        # Check authorization: owner or company owner
+        is_owner = session.user_id and str(post.user_id) == session.user_id
+        is_company_owner = False
+        if not is_owner and session.account_type == "company" and session.company_id:
+            profile = await db.get_profile(post.user_id)
+            if profile and profile.company_id and str(profile.company_id) == session.company_id:
+                is_company_owner = True
+        if not is_owner and not is_company_owner:
+            raise HTTPException(status_code=403, detail="Not authorized")
+
+        # Get current media items (convert to dicts with JSON-serializable datetime)
+        media_items = [
+            item.model_dump(mode='json') if hasattr(item, 'model_dump') else (item.dict() if hasattr(item, 'dict') else item)
+            for item in (post.media_items or [])
+        ]
+
+        # Validate: Max 3 items
+        if len(media_items) >= 3:
+            raise HTTPException(status_code=400, detail="Maximal 3 Medien erlaubt")
+
+        # Read file from form data
+        form = await request.form()
+        file = form.get("file") or form.get("image")  # Support both 'file' and 'image' keys
+        if not file or not hasattr(file, "read"):
+            raise HTTPException(status_code=400, detail="No file provided")
+
+        file_content = await file.read()
+        content_type = file.content_type or "application/octet-stream"
+
+        # Validate media type consistency (no mixing)
+        is_video = content_type.startswith("video/")
+        has_videos = any(item.get("type") == "video" for item in media_items)
+        has_images = any(item.get("type") == "image" for item in media_items)
+
+        if (is_video and has_images) or (not is_video and has_videos):
+            raise HTTPException(status_code=400, detail="Kann nicht Bilder und Videos mischen")
+
+        # Only allow 1 video max
+        if is_video and len(media_items) > 0:
+            raise HTTPException(status_code=400, detail="Nur 1 Video pro Post erlaubt")
+
+        # Upload to storage
+        media_url = await storage.upload_media(
+            file_content=file_content,
+            content_type=content_type,
+            user_id=str(post.user_id),
+        )
+
+        # Add to array
+        new_item = {
+            "type": "video" if is_video else "image",
+            "url": media_url,
+            "order": len(media_items),
+            "content_type": content_type,
+            "uploaded_at": datetime.now(timezone.utc).isoformat(),
+            "metadata": None
+        }
+        media_items.append(new_item)
+
+        # Update DB
+        await db.update_generated_post(UUID(post_id), {"media_items": media_items})
+
+        # Also update image_url for backward compatibility (first image)
+        if new_item["type"] == "image" and len([i for i in media_items if i["type"] == "image"]) == 1:
+            await db.update_generated_post(UUID(post_id), {"image_url": media_url})
+
+        return {"success": True, "media_item": new_item, "media_items": media_items}
+
+    except HTTPException:
+        raise
+    except ValueError as e:
+        raise HTTPException(status_code=400, detail=str(e))
+    except Exception as e:
+        logger.exception(f"Failed to upload post media: {e}")
+        raise HTTPException(status_code=500, detail=str(e))
+
+
+@user_router.delete("/api/posts/{post_id}/media/{media_index}")
+async def delete_post_media(request: Request, post_id: str, media_index: int):
+    """Delete a specific media item by index."""
+    session = require_user_session(request)
+    if not session:
+        raise HTTPException(status_code=401, detail="Not authenticated")
+
+    try:
+        post = await db.get_generated_post(UUID(post_id))
+        if not post:
+            raise HTTPException(status_code=404, detail="Post not found")
+
+        # Check authorization: owner or company owner
+        is_owner = session.user_id and str(post.user_id) == session.user_id
+        is_company_owner = False
+        if not is_owner and session.account_type == "company" and session.company_id:
+            profile = await db.get_profile(post.user_id)
+            if profile and profile.company_id and str(profile.company_id) == session.company_id:
+                is_company_owner = True
+        if not is_owner and not is_company_owner:
+            raise HTTPException(status_code=403, detail="Not authorized")
+
+        # Get current media items (convert to dicts with JSON-serializable datetime)
+        media_items = [
+            item.model_dump(mode='json') if hasattr(item, 'model_dump') else (item.dict() if hasattr(item, 'dict') else item)
+            for item in (post.media_items or [])
+        ]
+
+        if media_index < 0 or media_index >= len(media_items):
+            raise HTTPException(status_code=404, detail="Media item nicht gefunden")
+
+        # Delete from storage
+        item_to_delete = media_items[media_index]
+        try:
+            await storage.delete_image(item_to_delete["url"])
+        except Exception as e:
+            logger.warning(f"Failed to delete media from storage: {e}")
+
+        # Remove and re-index
+        media_items.pop(media_index)
+        for i, item in enumerate(media_items):
+            item["order"] = i
+
+        # Update DB
+        await db.update_generated_post(UUID(post_id), {"media_items": media_items})
+
+        # Update image_url for backward compatibility
+        first_image = next((item for item in media_items if item["type"] == "image"), None)
+        await db.update_generated_post(UUID(post_id), {"image_url": first_image["url"] if first_image else None})
+
+        return {"success": True, "media_items": media_items}
+
+    except HTTPException:
+        raise
+    except Exception as e:
+        logger.exception(f"Failed to delete post media: {e}")
+        raise HTTPException(status_code=500, detail=str(e))
+
+
+@user_router.put("/api/posts/{post_id}/media/reorder")
+async def reorder_post_media(request: Request, post_id: str):
+    """Reorder media items. Expects JSON: {"order": [2, 0, 1]}"""
+    session = require_user_session(request)
+    if not session:
+        raise HTTPException(status_code=401, detail="Not authenticated")
+
+    try:
+        post = await db.get_generated_post(UUID(post_id))
+        if not post:
+            raise HTTPException(status_code=404, detail="Post not found")
+
+        # Check authorization: owner or company owner
+        is_owner = session.user_id and str(post.user_id) == session.user_id
+        is_company_owner = False
+        if not is_owner and session.account_type == "company" and session.company_id:
+            profile = await db.get_profile(post.user_id)
+            if profile and profile.company_id and str(profile.company_id) == session.company_id:
+                is_company_owner = True
+        if not is_owner and not is_company_owner:
+            raise HTTPException(status_code=403, detail="Not authorized")
+
+        # Get current media items (convert to dicts with JSON-serializable datetime)
+        media_items = [
+            item.model_dump(mode='json') if hasattr(item, 'model_dump') else (item.dict() if hasattr(item, 'dict') else item)
+            for item in (post.media_items or [])
+        ]
+
+        # Parse request body
+        body = await request.json()
+        new_order = body.get("order", [])
+
+        # Validate order array
+        if len(new_order) != len(media_items) or set(new_order) != set(range(len(media_items))):
+            raise HTTPException(status_code=400, detail="Invalid order indices")
+
+        # Reorder
+        reordered = [media_items[i] for i in new_order]
+        for i, item in enumerate(reordered):
+            item["order"] = i
+
+        # Update DB
+        await db.update_generated_post(UUID(post_id), {"media_items": reordered})
+
+        return {"success": True, "media_items": reordered}
+
+    except HTTPException:
+        raise
+    except Exception as e:
+        logger.exception(f"Failed to reorder post media: {e}")
+        raise HTTPException(status_code=500, detail=str(e))
+
+
 # ==================== IMAGE PROXY FOR HTTPS ====================
 
 @user_router.get("/proxy/image/{bucket}/{path:path}")