diff --git a/client/src/components/Chat/Messages/Content/FilePreviewDialog.tsx b/client/src/components/Chat/Messages/Content/FilePreviewDialog.tsx
index 3860717c6c..113c4a9a83 100644
--- a/client/src/components/Chat/Messages/Content/FilePreviewDialog.tsx
+++ b/client/src/components/Chat/Messages/Content/FilePreviewDialog.tsx
@@ -94,37 +94,52 @@ function formatBytes(bytes: number): string {
   return `${bytes} B`;
 }
 
-function getDisplayType(fileType?: string, fileName?: string): string {
-  if (fileType) {
-    if (fileType.includes('pdf')) {
-      return 'PDF';
-    }
-    if (fileType.includes('word') || fileType.includes('document')) {
-      return 'Document';
-    }
-    if (fileType.includes('spreadsheet') || fileType.includes('excel')) {
-      return 'Spreadsheet';
-    }
-    if (fileType.includes('presentation') || fileType.includes('powerpoint')) {
-      return 'Presentation';
-    }
-    if (fileType.includes('image')) {
-      return 'Image';
-    }
-    if (fileType.startsWith('text/')) {
-      return fileType.split('/')[1]?.toUpperCase() || 'Text';
-    }
-    if (fileType.includes('json')) {
-      return 'JSON';
-    }
-    if (fileType.includes('xml')) {
-      return 'XML';
-    }
+function getMimeDisplayType(fileType?: string): string | undefined {
+  if (!fileType) {
+    return undefined;
   }
+  if (fileType.includes('pdf')) {
+    return 'PDF';
+  }
+  if (fileType.includes('word') || fileType.includes('document')) {
+    return 'Document';
+  }
+  if (fileType.includes('spreadsheet') || fileType.includes('excel')) {
+    return 'Spreadsheet';
+  }
+  if (fileType.includes('presentation') || fileType.includes('powerpoint')) {
+    return 'Presentation';
+  }
+  if (fileType.includes('image')) {
+    return 'Image';
+  }
+  if (fileType.startsWith('text/')) {
+    return fileType.split('/')[1]?.toUpperCase() || 'Text';
+  }
+  if (fileType.includes('json')) {
+    return 'JSON';
+  }
+  if (fileType.includes('xml')) {
+    return 'XML';
+  }
+  return undefined;
+}
+
+function getDisplayType(fileType?: string, fileName?: string): string {
+  const mimeDisplayType = getMimeDisplayType(fileType);
+
+  if (mimeDisplayType) {
+    return mimeDisplayType;
+  }
+
   const ext = fileName ? getFileExtension(fileName) : '';
   return ext ? ext.toUpperCase() : 'File';
 }
 
+function createTextDownloadUrl(text: string, fileType?: string): string {
+  return URL.createObjectURL(new Blob([text], { type: fileType || 'text/plain' }));
+}
+
 export default function FilePreviewDialog({
   open,
   onOpenChange,
@@ -165,6 +180,69 @@ export default function FilePreviewDialog({
     return result.data?.status === 'ready' ? result.data.text : undefined;
   }, [fetchTextPreview, fileContent]);
 
+  const markPreviewUnavailable = useCallback(() => {
+    if (cancelledRef.current) {
+      return;
+    }
+    setPreviewError(true);
+  }, []);
+
+  const finishLoading = useCallback(() => {
+    loadingRef.current = false;
+
+    if (cancelledRef.current) {
+      return;
+    }
+    setLoading(false);
+  }, []);
+
+  const loadTextSourcePreview = useCallback(async () => {
+    const text = await getTextSourceContent();
+
+    if (cancelledRef.current) {
+      return;
+    }
+    if (text == null) {
+      markPreviewUnavailable();
+      return;
+    }
+    setFileContent(text);
+  }, [getTextSourceContent, markPreviewUnavailable]);
+
+  const loadStoredPreview = useCallback(async () => {
+    const result = await downloadFile();
+
+    if (cancelledRef.current) {
+      return;
+    }
+    if (!result.data) {
+      markPreviewUnavailable();
+      return;
+    }
+
+    const resp = await fetch(result.data);
+    const blob = await resp.blob();
+
+    if (cancelledRef.current) {
+      return;
+    }
+    if (previewKind === 'text') {
+      setFileContent(await blob.text());
+      return;
+    }
+
+    const typed = new Blob([blob], { type: 'application/pdf' });
+    setFileBlobUrl(URL.createObjectURL(typed));
+  }, [downloadFile, markPreviewUnavailable, previewKind]);
+
+  const loadPreviewContent = useCallback(async () => {
+    if (isTextSource) {
+      await loadTextSourcePreview();
+      return;
+    }
+    await loadStoredPreview();
+  }, [isTextSource, loadStoredPreview, loadTextSourcePreview]);
+
   const loadPreview = useCallback(async () => {
     if (!fileId || !previewKind || loadingRef.current) {
       return;
@@ -175,101 +253,74 @@ export default function FilePreviewDialog({
     setPreviewError(false);
 
     try {
-      if (isTextSource) {
-        const text = await getTextSourceContent();
-        if (cancelledRef.current || text == null) {
-          if (!cancelledRef.current) {
-            setPreviewError(true);
-          }
-          return;
-        }
-        setFileContent(text);
-        return;
-      }
-
-      const result = await downloadFile();
-      if (cancelledRef.current || !result.data) {
-        if (!cancelledRef.current) {
-          setPreviewError(true);
-        }
-        return;
-      }
-
-      const resp = await fetch(result.data);
-      const blob = await resp.blob();
-
-      if (cancelledRef.current) {
-        return;
-      }
-
-      if (previewKind === 'text') {
-        setFileContent(await blob.text());
-      } else {
-        const typed = new Blob([blob], { type: 'application/pdf' });
-        setFileBlobUrl(URL.createObjectURL(typed));
-      }
+      await loadPreviewContent();
     } catch {
-      if (!cancelledRef.current) {
-        setPreviewError(true);
-      }
+      markPreviewUnavailable();
     } finally {
-      loadingRef.current = false;
-      if (!cancelledRef.current) {
-        setLoading(false);
-      }
+      finishLoading();
     }
-  }, [fileId, previewKind, isTextSource, getTextSourceContent, downloadFile]);
+  }, [fileId, finishLoading, loadPreviewContent, markPreviewUnavailable, previewKind]);
+
+  const downloadTextSourceFile = useCallback(async () => {
+    const text = await getTextSourceContent();
+
+    if (text == null) {
+      return;
+    }
+    triggerDownload(createTextDownloadUrl(text, fileType), fileName);
+  }, [fileName, fileType, getTextSourceContent]);
+
+  const downloadStoredFile = useCallback(async () => {
+    const result = await downloadFile();
+
+    if (!result.data) {
+      return;
+    }
+    triggerDownload(result.data, fileName);
+  }, [downloadFile, fileName]);
 
   const handleDownload = useCallback(async () => {
     if (!fileId) {
       return;
     }
+
     try {
       if (isTextSource) {
-        const text = await getTextSourceContent();
-        if (text == null) {
-          return;
-        }
-        const downloadURL = URL.createObjectURL(
-          new Blob([text], { type: fileType || 'text/plain' }),
-        );
-        triggerDownload(downloadURL, fileName);
+        await downloadTextSourceFile();
         return;
       }
-
-      const result = await downloadFile();
-      if (!result.data) {
-        return;
-      }
-      triggerDownload(result.data, fileName);
+      await downloadStoredFile();
     } catch (err) {
       logger.error('[FilePreviewDialog] Download failed:', err);
     }
-  }, [downloadFile, fileId, fileName, fileType, isTextSource, getTextSourceContent]);
+  }, [downloadStoredFile, downloadTextSourceFile, fileId, isTextSource]);
 
   useEffect(() => {
-    if (open && previewKind && !fileContent && !fileBlobUrl) {
-      loadPreview();
+    if (!open || !previewKind || fileContent || fileBlobUrl) {
+      return;
     }
+    loadPreview();
   }, [open, previewKind, fileContent, fileBlobUrl, loadPreview]);
 
   useEffect(() => {
     return () => {
-      if (fileBlobUrl) {
-        URL.revokeObjectURL(fileBlobUrl);
+      if (!fileBlobUrl) {
+        return;
       }
+      URL.revokeObjectURL(fileBlobUrl);
     };
   }, [fileBlobUrl]);
 
   useEffect(() => {
-    if (!open) {
-      cancelledRef.current = true;
-      setFileContent(null);
-      setFileBlobUrl(null);
-      setPreviewError(false);
-      setLoading(false);
-      setIsCopied(false);
+    if (open) {
+      return;
     }
+    cancelledRef.current = true;
+    setFileContent(null);
+    setFileBlobUrl(null);
+    setPreviewError(false);
+    setLoading(false);
+    setIsCopied(false);
   }, [open]);
 
   const handleCopy = useCallback(() => {
diff --git a/client/src/components/Chat/Messages/Content/Files.tsx b/client/src/components/Chat/Messages/Content/Files.tsx
index a667cae736..fe422af0b8 100644
--- a/client/src/components/Chat/Messages/Content/Files.tsx
+++ b/client/src/components/Chat/Messages/Content/Files.tsx
@@ -5,50 +5,91 @@ import FileContainer from '~/components/Chat/Input/Files/FileContainer';
 import FilePreviewDialog from './FilePreviewDialog';
 import Image from './Image';
 
+type MessageFile = Partial<TFile>;
+
+type SplitMessageFiles = {
+  imageFiles: MessageFile[];
+  otherFiles: MessageFile[];
+};
+
 const isUploadAsTextAttachment = (file: Partial<TFile>) =>
   file.source === FileSources.text && file.context === FileContext.message_attachment;
 
-const Files = ({ message }: { message?: TMessage }) => {
-  const imageFiles = useMemo(() => {
-    return message?.files?.filter((file) => file.type?.startsWith('image/')) || [];
-  }, [message?.files]);
+const splitMessageFiles = (files?: MessageFile[]): SplitMessageFiles => {
+  if (!files?.length) {
+    return { imageFiles: [], otherFiles: [] };
+  }
 
-  const otherFiles = useMemo(() => {
-    return message?.files?.filter((file) => !file.type?.startsWith('image/')) || [];
-  }, [message?.files]);
+  return files.reduce<SplitMessageFiles>(
+    (acc, file) => {
+      const bucket = file.type?.startsWith('image/') === true ? acc.imageFiles : acc.otherFiles;
+      bucket.push(file);
+      return acc;
+    },
+    { imageFiles: [], otherFiles: [] },
+  );
+};
+
+const getMessageFileKey = (file: MessageFile, index: number) =>
+  file.file_id ?? `${file.filename ?? 'file'}-${index}`;
+
+const MessageFileContainer = ({
+  file,
+  onSelect,
+}: {
+  file: MessageFile;
+  onSelect: (file: MessageFile) => void;
+}) => {
+  const previewDisabled = isUploadAsTextAttachment(file);
+  const handleClick = useCallback(() => onSelect(file), [file, onSelect]);
+
+  return (
+    <FileContainer
+      file={file as TFile}
+      disabled={previewDisabled}
+      onClick={previewDisabled ? undefined : handleClick}
+    />
+  );
+};
+
+const MessageImage = ({ file }: { file: MessageFile }) => (
+  <Image
+    imagePath={file.preview ?? file.filepath ?? ''}
+    height={file.height ?? 1920}
+    width={file.width ?? 1080}
+    altText={file.filename ?? 'Uploaded Image'}
+  />
+);
+
+const Files = ({ message }: { message?: TMessage }) => {
+  const { imageFiles, otherFiles } = useMemo(
+    () => splitMessageFiles(message?.files),
+    [message?.files],
+  );
 
   const [selectedFile, setSelectedFile] = useState<Partial<TFile> | null>(null);
 
   const handleClose = useCallback((open: boolean) => {
-    if (!open) {
-      setSelectedFile(null);
+    if (open) {
+      return;
     }
+    setSelectedFile(null);
   }, []);
 
+  const handleSelect = useCallback((file: MessageFile) => setSelectedFile(file), []);
+
   return (
     <>
-      {otherFiles.length > 0 &&
-        otherFiles.map((file) => {
-          const previewDisabled = isUploadAsTextAttachment(file);
-          return (
-            <FileContainer
-              key={file.file_id}
-              file={file as TFile}
-              disabled={previewDisabled}
-              onClick={previewDisabled ? undefined : () => setSelectedFile(file)}
-            />
-          );
-        })}
-      {imageFiles.length > 0 &&
-        imageFiles.map((file) => (
-          <Image
-            key={file.file_id}
-            imagePath={file.preview ?? file.filepath ?? ''}
-            height={file.height ?? 1920}
-            width={file.width ?? 1080}
-            altText={file.filename ?? 'Uploaded Image'}
-          />
-        ))}
+      {otherFiles.map((file, index) => (
+        <MessageFileContainer
+          key={getMessageFileKey(file, index)}
+          file={file}
+          onSelect={handleSelect}
+        />
+      ))}
+      {imageFiles.map((file, index) => (
+        <MessageImage key={getMessageFileKey(file, index)} file={file} />
+      ))}
       <FilePreviewDialog
         open={selectedFile !== null}
         onOpenChange={handleClose}