feat(image): Improve image attachment loading and error handling

lib/core/services/conversation_parsing.dart

@@ -280,6 +280,9 @@ Map<String, dynamic>? _parseSiblingAsVersion(
         };
         if (entry['name'] != null) fileMap['name'] = entry['name'];
         if (entry['size'] != null) fileMap['size'] = entry['size'];
+        if (entry['content_type'] != null) {
+          fileMap['content_type'] = entry['content_type'];
+        }
         allFiles.add(fileMap);
       }
     }
@@ -448,6 +451,9 @@ Map<String, dynamic> _parseOpenWebUIMessageToJson(
         };
         if (entry['name'] != null) fileMap['name'] = entry['name'];
         if (entry['size'] != null) fileMap['size'] = entry['size'];
+        if (entry['content_type'] != null) {
+          fileMap['content_type'] = entry['content_type'];
+        }
         final headers = _coerceStringMap(entry['headers']);
         if (headers != null && headers.isNotEmpty) {
           fileMap['headers'] = headers;
@@ -455,12 +461,22 @@ Map<String, dynamic> _parseOpenWebUIMessageToJson(
         allFiles.add(fileMap);
 
         final url = entry['url'].toString();
-        // Handle both URL formats: /api/v1/files/{id} and /api/v1/files/{id}/content
+        // Handle all URL formats:
+        // 1. /api/v1/files/{id} and /api/v1/files/{id}/content (old format)
+        // 2. Just a file ID like "abc-123-def" (new OpenWebUI format)
         final match = RegExp(
           r'/api/v1/files/([^/]+)(?:/content)?$',
         ).firstMatch(url);
         if (match != null) {
           attachments.add(match.group(1)!);
+        } else if (!url.startsWith('data:') &&
+            !url.startsWith('http') &&
+            !url.startsWith('/')) {
+          // New format: URL is just a bare file ID (UUID-like)
+          // Validate it looks like a reasonable ID (not an empty string)
+          if (url.isNotEmpty) {
+            attachments.add(url);
+          }
         }
       }
     }

lib/features/chat/providers/chat_providers.dart

@@ -1092,7 +1092,8 @@ Future<Map<String, dynamic>> _buildMessagePayloadWithAttachments({
         allFiles.add({
           'type': 'file',
           'id': attachmentId,
-          'url': '/api/v1/files/$attachmentId',
+          // OpenWebUI now stores just the file ID, not the full URL path
+          'url': attachmentId,
           'name': fileName,
           if (fileSize != null) 'size': fileSize,
         });
@@ -1801,7 +1802,9 @@ Future<void> _sendMessageInternal(
           'type': isImage ? 'image' : 'file',
           'id': fileId,
           'name': fileName,
-          'url': '/api/v1/files/$fileId', // Full URL for conversation parsing compatibility
+          // OpenWebUI now stores just the file ID, not the full URL path
+          // The frontend resolves it when displaying
+          'url': fileId,
           if (fileSize != null) 'size': fileSize,
           if (collectionName != null) 'collection_name': collectionName,
           if (contentType.isNotEmpty) 'content_type': contentType,
@@ -1811,7 +1814,7 @@ Future<void> _sendMessageInternal(
           'type': 'file',
           'id': fileId,
           'name': 'file',
-          'url': '/api/v1/files/$fileId',
+          'url': fileId,
         };
       }
     });

lib/features/chat/utils/file_utils.dart

@@ -0,0 +1,22 @@
+// Utility functions for handling file data in chat messages.
+// Used by both user and assistant message widgets.
+
+/// Checks if a file map represents an image.
+/// Matches OpenWebUI behavior: type === 'image' OR content_type starts with 'image/'
+bool isImageFile(dynamic file) {
+  if (file is! Map) return false;
+  if (file['type'] == 'image') return true;
+  final contentType = file['content_type']?.toString() ?? '';
+  return contentType.startsWith('image/');
+}
+
+/// Extracts the file URL or ID from a file map.
+/// OpenWebUI stores either a full URL, data URL, or just the file ID.
+/// 
+/// Returns the URL/ID string, or null if the file has no valid URL.
+String? getFileUrl(dynamic file) {
+  if (file is! Map) return null;
+  final url = file['url'];
+  if (url == null) return null;
+  return url.toString();
+}

lib/features/chat/widgets/assistant_message_widget.dart

@@ -27,6 +27,7 @@ import 'sources/openwebui_sources.dart';
 import '../providers/assistant_response_builder_provider.dart';
 import '../../../core/services/worker_manager.dart';
 import 'streaming_status_widget.dart';
+import '../utils/file_utils.dart';
 
 // Pre-compiled regex patterns for image processing (performance optimization)
 final _base64ImagePattern = RegExp(r'data:image/[^;]+;base64,[A-Za-z0-9+/]+=*');
@@ -1119,12 +1120,9 @@ class _AssistantMessageWidgetState extends ConsumerState<AssistantMessageWidget>
     final allFiles = filesArray;
 
     // Separate images and non-image files
-    final imageFiles = allFiles
+    // Match OpenWebUI: type === 'image' OR content_type starts with 'image/'
-        .where((file) => file['type'] == 'image')
+    final imageFiles = allFiles.where(isImageFile).toList();
-        .toList();
+    final nonImageFiles = allFiles.where((file) => !isImageFile(file)).toList();
-    final nonImageFiles = allFiles
-        .where((file) => file['type'] != 'image')
-        .toList();
 
     final widgets = <Widget>[];
 
@@ -1164,7 +1162,7 @@ class _AssistantMessageWidgetState extends ConsumerState<AssistantMessageWidget>
               key: ValueKey('file_single_${imageFiles[0]['url']}'),
               child: Builder(
                 builder: (context) {
-                  final imageUrl = imageFiles[0]['url'] as String?;
+                  final imageUrl = getFileUrl(imageFiles[0]);
                   if (imageUrl == null) return const SizedBox.shrink();
 
                   return EnhancedImageAttachment(
@@ -1189,7 +1187,7 @@ class _AssistantMessageWidgetState extends ConsumerState<AssistantMessageWidget>
               spacing: Spacing.sm,
               runSpacing: Spacing.sm,
               children: imageFiles.map<Widget>((file) {
-                final imageUrl = file['url'] as String?;
+                final imageUrl = getFileUrl(file);
                 if (imageUrl == null) return const SizedBox.shrink();
 
                 return EnhancedImageAttachment(
@@ -1232,12 +1230,13 @@ class _AssistantMessageWidgetState extends ConsumerState<AssistantMessageWidget>
       spacing: Spacing.sm,
       runSpacing: Spacing.sm,
       children: nonImageFiles.map<Widget>((file) {
-        final fileUrl = file['url'] as String?;
+        final fileUrl = getFileUrl(file);
-
         if (fileUrl == null) return const SizedBox.shrink();
 
-        // Extract file ID from URL - handle both formats:
+        // Extract file ID from URL - handle formats:
-        // /api/v1/files/{id} and /api/v1/files/{id}/content
+        // - Bare file ID (new OpenWebUI format): "abc-123-def"
+        // - /api/v1/files/{id} (legacy format)
+        // - /api/v1/files/{id}/content (legacy format)
         String attachmentId = fileUrl;
         if (fileUrl.contains('/api/v1/files/')) {
           final fileIdMatch = _fileIdPattern.firstMatch(fileUrl);

lib/features/chat/widgets/enhanced_image_attachment.dart

@@ -30,6 +30,8 @@ final _base64WhitespacePattern = RegExp(r'\s');
 /// Call this with the server file ID and image bytes after successful upload.
 void preCacheImageBytes(String fileId, Uint8List bytes) {
   if (fileId.isEmpty || bytes.isEmpty) return;
+  // Clear any previous error state for this file
+  _globalErrorStates.remove(fileId);
   _globalImageBytesCache[fileId] = bytes;
   _globalLoadingStates[fileId] = false;
   // Detect SVG
@@ -132,8 +134,8 @@ class _EnhancedImageAttachmentState
   String? _errorMessage;
   bool _isDecoding = false;
   bool _isSvg = false;
-  late final String _heroTag;
+  late String _heroTag;
-  // Removed unused animation and state flags
+  bool _hasAttemptedLoad = false;
 
   @override
   bool get wantKeepAlive => true;
@@ -150,12 +152,40 @@ class _EnhancedImageAttachmentState
     });
   }
 
+  @override
+  void didUpdateWidget(covariant EnhancedImageAttachment oldWidget) {
+    super.didUpdateWidget(oldWidget);
+    // If the attachment ID changed, reload the image
+    if (oldWidget.attachmentId != widget.attachmentId) {
+      _heroTag = 'image_${widget.attachmentId}_${identityHashCode(this)}';
+      // Reset local state with setState for immediate visual feedback
+      setState(() {
+        _cachedImageData = null;
+        _cachedBytes = null;
+        _hasAttemptedLoad = false;
+        _isLoading = true;
+        _errorMessage = null;
+        _isDecoding = false;
+        _isSvg = false;
+      });
+      // Load the new image
+      WidgetsBinding.instance.addPostFrameCallback((_) {
+        if (!mounted) return;
+        _loadImage();
+      });
+    }
+  }
+
   @override
   void dispose() {
     super.dispose();
   }
 
   Future<void> _loadImage() async {
+    // Prevent duplicate loads
+    if (_hasAttemptedLoad) return;
+    _hasAttemptedLoad = true;
+
     final l10n = AppLocalizations.of(context)!;
 
     // Check bytes cache first (populated during upload for instant display)
@@ -172,6 +202,8 @@ class _EnhancedImageAttachmentState
       return;
     }
 
+    // Check for cached errors - if image previously failed, show error immediately
+    // Note: preCacheImageBytes() clears errors when upload completes successfully
     final cachedError = _globalErrorStates[widget.attachmentId];
     if (cachedError != null) {
       if (mounted) {
@@ -407,8 +439,16 @@ class _EnhancedImageAttachmentState
       return _buildErrorState();
     }
 
-    if (_cachedImageData == null) {
+    if (_cachedImageData == null && _cachedBytes == null) {
-      return const SizedBox.shrink();
+      // No data available - this shouldn't happen in normal flow since
+      // _loadImage always sets either data, bytes, or error before completing.
+      // Show error state rather than attempting reload from build().
+      return _buildErrorState();
+    }
+
+    // If we have bytes but no cached data string, use bytes directly
+    if (_cachedImageData == null && _cachedBytes != null) {
+      return _isSvg ? _buildBase64Svg() : _buildBase64Image();
     }
 
     // Handle different image data formats
@@ -692,11 +732,15 @@ class _EnhancedImageAttachmentState
   }
 
   void _showFullScreenImage(BuildContext context) {
+    // Handle both data URL string and raw bytes cases
+    if (_cachedImageData == null && _cachedBytes == null) return;
+
     Navigator.of(context).push(
       MaterialPageRoute(
         fullscreenDialog: true,
         builder: (context) => FullScreenImageViewer(
-          imageData: _cachedImageData!,
+          imageData: _cachedImageData,
+          imageBytes: _cachedBytes,
           tag: _heroTag,
           isSvg: _isSvg,
           customHeaders: widget.httpHeaders,
@@ -707,31 +751,56 @@ class _EnhancedImageAttachmentState
 }
 
 class FullScreenImageViewer extends ConsumerWidget {
-  final String imageData;
+  /// Image data as a URL (http://) or data URL (data:image/...) or base64 string.
+  /// Either this or [imageBytes] must be provided.
+  final String? imageData;
+
+  /// Raw image bytes. Used when [imageData] is null.
+  final Uint8List? imageBytes;
+
   final String tag;
   final bool isSvg;
   final Map<String, String>? customHeaders;
 
   const FullScreenImageViewer({
     super.key,
-    required this.imageData,
+    this.imageData,
+    this.imageBytes,
     required this.tag,
     this.isSvg = false,
     this.customHeaders,
-  });
+  }) : assert(imageData != null || imageBytes != null,
+            'Either imageData or imageBytes must be provided');
 
   @override
   Widget build(BuildContext context, WidgetRef ref) {
     Widget imageWidget;
 
-    if (imageData.startsWith('http')) {
+    // If we have raw bytes, use them directly
+    if (imageData == null && imageBytes != null) {
+      if (isSvg || _isSvgBytes(imageBytes!)) {
+        imageWidget = SvgPicture.memory(
+          imageBytes!,
+          fit: BoxFit.contain,
+          errorBuilder: (context, error, stackTrace) => Center(
+            child: Icon(
+              Icons.error_outline,
+              color: context.conduitTheme.error,
+              size: 48,
+            ),
+          ),
+        );
+      } else {
+        imageWidget = Image.memory(imageBytes!, fit: BoxFit.contain);
+      }
+    } else if (imageData != null && imageData!.startsWith('http')) {
       // Get authentication headers if available
       final defaultHeaders = buildImageHeadersFromWidgetRef(ref);
       final headers = _mergeHeaders(defaultHeaders, customHeaders);
 
-      if (isSvg || _isSvgUrl(imageData)) {
+      if (isSvg || _isSvgUrl(imageData!)) {
         imageWidget = SvgPicture.network(
-          imageData,
+          imageData!,
           fit: BoxFit.contain,
           headers: headers,
           placeholderBuilder: (context) => Center(
@@ -750,7 +819,7 @@ class FullScreenImageViewer extends ConsumerWidget {
       } else {
         final cacheManager = ref.watch(selfSignedImageCacheManagerProvider);
         imageWidget = CachedNetworkImage(
-          imageUrl: imageData,
+          imageUrl: imageData!,
           fit: BoxFit.contain,
           cacheManager: cacheManager,
           httpHeaders: headers,
@@ -768,24 +837,24 @@ class FullScreenImageViewer extends ConsumerWidget {
           ),
         );
       }
-    } else {
+    } else if (imageData != null) {
       try {
         String actualBase64;
-        if (imageData.startsWith('data:')) {
+        if (imageData!.startsWith('data:')) {
-          final commaIndex = imageData.indexOf(',');
+          final commaIndex = imageData!.indexOf(',');
           if (commaIndex == -1) {
             throw const FormatException('Invalid data URI');
           }
-          actualBase64 = imageData.substring(commaIndex + 1);
+          actualBase64 = imageData!.substring(commaIndex + 1);
         } else {
-          actualBase64 = imageData;
+          actualBase64 = imageData!;
         }
-        final imageBytes = base64.decode(actualBase64);
+        final decodedBytes = base64.decode(actualBase64);
 
         // Check if SVG content
-        if (isSvg || _isSvgDataUrl(imageData) || _isSvgBytes(imageBytes)) {
+        if (isSvg || _isSvgDataUrl(imageData!) || _isSvgBytes(decodedBytes)) {
           imageWidget = SvgPicture.memory(
-            imageBytes,
+            decodedBytes,
             fit: BoxFit.contain,
             errorBuilder: (context, error, stackTrace) => Center(
               child: Icon(
@@ -796,7 +865,7 @@ class FullScreenImageViewer extends ConsumerWidget {
             ),
           );
         } else {
-          imageWidget = Image.memory(imageBytes, fit: BoxFit.contain);
+          imageWidget = Image.memory(decodedBytes, fit: BoxFit.contain);
         }
       } catch (e) {
         imageWidget = Center(
@@ -807,6 +876,15 @@ class FullScreenImageViewer extends ConsumerWidget {
           ),
         );
       }
+    } else {
+      // No image data available - show error
+      imageWidget = Center(
+        child: Icon(
+          Icons.error_outline,
+          color: context.conduitTheme.error,
+          size: 48,
+        ),
+      );
     }
 
     final tokens = context.colorTokens;
@@ -860,7 +938,11 @@ class FullScreenImageViewer extends ConsumerWidget {
       Uint8List bytes;
       String? fileExtension;
 
-      if (imageData.startsWith('http')) {
+      // If we have raw bytes, use them directly
+      if (imageData == null && imageBytes != null) {
+        bytes = imageBytes!;
+        fileExtension = isSvg ? 'svg' : 'png';
+      } else if (imageData!.startsWith('http')) {
         final api = ref.read(apiServiceProvider);
         final authToken = ref.read(authTokenProvider3);
         final headers = <String, String>{};
@@ -878,7 +960,7 @@ class FullScreenImageViewer extends ConsumerWidget {
 
         final client = api?.dio ?? dio.Dio();
         final response = await client.get<List<int>>(
-          imageData,
+          imageData!,
           options: dio.Options(
             responseType: dio.ResponseType.bytes,
             headers: mergedHeaders,
@@ -895,7 +977,7 @@ class FullScreenImageViewer extends ConsumerWidget {
           fileExtension = contentType.split('/').last;
           if (fileExtension == 'jpeg') fileExtension = 'jpg';
         } else {
-          final uri = Uri.tryParse(imageData);
+          final uri = Uri.tryParse(imageData!);
           final lastSegment = uri?.pathSegments.isNotEmpty == true
               ? uri!.pathSegments.last
               : '';
@@ -907,20 +989,23 @@ class FullScreenImageViewer extends ConsumerWidget {
             }
           }
         }
-      } else {
+      } else if (imageData != null) {
-        String actualBase64 = imageData;
+        String actualBase64 = imageData!;
-        if (imageData.startsWith('data:')) {
+        if (imageData!.startsWith('data:')) {
-          final commaIndex = imageData.indexOf(',');
+          final commaIndex = imageData!.indexOf(',');
-          final meta = imageData.substring(5, commaIndex); // image/png;base64
+          final meta = imageData!.substring(5, commaIndex); // image/png;base64
           final slashIdx = meta.indexOf('/');
           final semicolonIdx = meta.indexOf(';');
           if (slashIdx != -1 && semicolonIdx != -1 && slashIdx < semicolonIdx) {
             final subtype = meta.substring(slashIdx + 1, semicolonIdx);
             fileExtension = subtype == 'jpeg' ? 'jpg' : subtype;
           }
-          actualBase64 = imageData.substring(commaIndex + 1);
+          actualBase64 = imageData!.substring(commaIndex + 1);
         }
         bytes = base64.decode(actualBase64);
+      } else {
+        // No image data available
+        return;
       }
 
       fileExtension ??= 'png';

lib/features/chat/widgets/user_message_bubble.dart

@@ -13,6 +13,7 @@ import '../providers/chat_providers.dart';
 import '../../../shared/services/tasks/task_queue.dart';
 import '../../../shared/utils/conversation_context_menu.dart';
 import '../../tools/providers/tools_providers.dart';
+import '../utils/file_utils.dart';
 
 // Pre-compiled regex for extracting file IDs from URLs (performance optimization)
 // Handles both /api/v1/files/{id} and /api/v1/files/{id}/content formats
@@ -84,16 +85,21 @@ class _UserMessageBubbleState extends ConsumerState<UserMessageBubble> {
     final allFiles = widget.message.files!;
 
     // Separate images and non-image files
+    // Match OpenWebUI: type === 'image' OR content_type starts with 'image/'
     final imageFiles = allFiles
         .where(
           (file) =>
-              file is Map && file['type'] == 'image' && file['url'] != null,
+              file is Map &&
+              isImageFile(file) &&
+              getFileUrl(file) != null,
         )
         .toList();
     final nonImageFiles = allFiles
         .where(
           (file) =>
-              file is Map && file['type'] != 'image' && file['url'] != null,
+              file is Map &&
+              !isImageFile(file) &&
+              getFileUrl(file) != null,
         )
         .toList();
 
@@ -131,7 +137,8 @@ class _UserMessageBubbleState extends ConsumerState<UserMessageBubble> {
   Widget _buildFileImageLayout(List<dynamic> imageFiles, int imageCount) {
     if (imageCount == 1) {
       final file = imageFiles[0];
-      final String imageUrl = file['url'] as String;
+      final imageUrl = getFileUrl(file);
+      if (imageUrl == null) return const SizedBox.shrink();
       return Row(
         key: ValueKey('user_file_single_$imageUrl'),
         mainAxisAlignment: MainAxisAlignment.end,
@@ -175,7 +182,8 @@ class _UserMessageBubbleState extends ConsumerState<UserMessageBubble> {
               children: imageFiles.asMap().entries.map((entry) {
                 final index = entry.key;
                 final file = entry.value;
-                final String imageUrl = file['url'] as String;
+                final imageUrl = getFileUrl(file);
+                if (imageUrl == null) return const SizedBox.shrink();
                 return Padding(
                   padding: EdgeInsets.only(left: index == 0 ? 0 : Spacing.xs),
                   child: Container(
@@ -223,7 +231,8 @@ class _UserMessageBubbleState extends ConsumerState<UserMessageBubble> {
                 spacing: Spacing.xs,
                 runSpacing: Spacing.xs,
                 children: imageFiles.map((file) {
-                  final String imageUrl = file['url'] as String;
+                  final imageUrl = getFileUrl(file);
+                  if (imageUrl == null) return const SizedBox.shrink();
                   return Container(
                     decoration: BoxDecoration(
                       borderRadius: BorderRadius.circular(AppBorderRadius.md),