From 5d78d66b00d9df9af23cd4121c5bd5d00caa5e60 Mon Sep 17 00:00:00 2001
From: tusharmagar <tushmag@gmail.com>
Date: Mon, 23 Feb 2026 12:01:03 +0530
Subject: [PATCH] Refactor chat message attachment handling and improve UI for
 attachments in chat input and sidebar

---
 apps/x/apps/renderer/src/App.tsx              |  27 +---
 .../components/chat-input-with-mentions.tsx   | 103 ++++++++++---
 .../components/chat-message-attachments.tsx   | 137 ++++++++++++++++++
 .../renderer/src/components/chat-sidebar.tsx  |  26 +---
 .../src/lib/attachment-presentation.ts        | 107 ++++++++++++++
 .../renderer/src/lib/chat-conversation.ts     |   1 +
 apps/x/apps/renderer/src/lib/file-utils.ts    |  18 +++
 7 files changed, 359 insertions(+), 60 deletions(-)
 create mode 100644 apps/x/apps/renderer/src/components/chat-message-attachments.tsx
 create mode 100644 apps/x/apps/renderer/src/lib/attachment-presentation.ts

diff --git a/apps/x/apps/renderer/src/App.tsx b/apps/x/apps/renderer/src/App.tsx
index 1eda1b44..63a0d3b4 100644
--- a/apps/x/apps/renderer/src/App.tsx
+++ b/apps/x/apps/renderer/src/App.tsx
@@ -5,12 +5,12 @@ import { RunEvent, ListRunsResponse } from '@x/shared/src/runs.js';
 import type { LanguageModelUsage, ToolUIPart } from 'ai';
 import './App.css'
 import z from 'zod';
-import { CheckIcon, LoaderIcon, Paperclip, PanelLeftIcon, Maximize2, Minimize2, ChevronLeftIcon, ChevronRightIcon, SquarePen, SearchIcon } from 'lucide-react';
-import { isImageMime } from '@/lib/file-utils'
+import { CheckIcon, LoaderIcon, PanelLeftIcon, Maximize2, Minimize2, ChevronLeftIcon, ChevronRightIcon, SquarePen, SearchIcon } from 'lucide-react';
 import { cn } from '@/lib/utils';
 import { MarkdownEditor } from './components/markdown-editor';
 import { ChatSidebar } from './components/chat-sidebar';
 import { ChatInputWithMentions, type StagedAttachment } from './components/chat-input-with-mentions';
+import { ChatMessageAttachments } from '@/components/chat-message-attachments'
 import { GraphView, type GraphEdge, type GraphNode } from '@/components/graph-view';
 import { useDebounce } from './hooks/use-debounce';
 import { SidebarContentPanel } from '@/components/sidebar-content';
@@ -1659,6 +1659,7 @@ function App() {
           filename: attachment.filename,
           mediaType: attachment.mediaType,
           size: attachment.size,
+          thumbnailUrl: attachment.thumbnailUrl,
         }))
       : undefined
     setConversation((prev) => [...prev, {
@@ -2951,24 +2952,12 @@ function App() {
         if (item.attachments && item.attachments.length > 0) {
           return (
             <Message key={item.id} from={item.role}>
-              <MessageContent>
-                <div className="flex flex-wrap gap-1.5 mb-2">
-                  {item.attachments.map((attachment, index) => (
-                    <span
-                      key={index}
-                      className="inline-flex items-center gap-1.5 text-xs bg-muted text-muted-foreground px-2 py-1 rounded-md"
-                    >
-                      {isImageMime(attachment.mediaType) ? (
-                        <span className="size-3 rounded bg-primary/20" />
-                      ) : (
-                        <Paperclip className="size-3" />
-                      )}
-                      {attachment.filename}
-                    </span>
-                  ))}
-                </div>
-                {item.content}
+              <MessageContent className="group-[.is-user]:bg-transparent group-[.is-user]:px-0 group-[.is-user]:py-0 group-[.is-user]:rounded-none">
+                <ChatMessageAttachments attachments={item.attachments} />
               </MessageContent>
+              {item.content && (
+                <MessageContent>{item.content}</MessageContent>
+              )}
             </Message>
           )
         }
diff --git a/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx b/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
index 4dfb174e..7ab65a45 100644
--- a/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
+++ b/apps/x/apps/renderer/src/components/chat-input-with-mentions.tsx
@@ -1,7 +1,27 @@
 import { useCallback, useEffect, useRef, useState } from 'react'
-import { ArrowUp, LoaderIcon, Paperclip, Plus, Square, X } from 'lucide-react'
+import {
+  ArrowUp,
+  AudioLines,
+  FileArchive,
+  FileCode2,
+  FileIcon,
+  FileSpreadsheet,
+  FileText,
+  FileVideo,
+  LoaderIcon,
+  Plus,
+  Square,
+  X,
+} from 'lucide-react'
 
 import { Button } from '@/components/ui/button'
+import {
+  type AttachmentIconKind,
+  getAttachmentDisplayName,
+  getAttachmentIconKind,
+  getAttachmentToneClass,
+  getAttachmentTypeLabel,
+} from '@/lib/attachment-presentation'
 import { getExtension, getFileDisplayName, getMimeFromExtension, isImageMime } from '@/lib/file-utils'
 import { cn } from '@/lib/utils'
 import {
@@ -25,6 +45,25 @@ export type StagedAttachment = {
 
 const MAX_ATTACHMENT_SIZE = 10 * 1024 * 1024 // 10MB
 
+function getAttachmentIcon(kind: AttachmentIconKind) {
+  switch (kind) {
+    case 'audio':
+      return AudioLines
+    case 'video':
+      return FileVideo
+    case 'spreadsheet':
+      return FileSpreadsheet
+    case 'archive':
+      return FileArchive
+    case 'code':
+      return FileCode2
+    case 'text':
+      return FileText
+    default:
+      return FileIcon
+  }
+}
+
 interface ChatInputInnerProps {
   onSubmit: (message: PromptInputMessage, mentions?: FileMention[], attachments?: StagedAttachment[]) => void
   onStop?: () => void
@@ -53,6 +92,7 @@ function ChatInputInner({
   const controller = usePromptInputController()
   const message = controller.textInput.value
   const [attachments, setAttachments] = useState<StagedAttachment[]>([])
+  const [focusNonce, setFocusNonce] = useState(0)
   const fileInputRef = useRef<HTMLInputElement>(null)
   const canSubmit = (Boolean(message.trim()) || attachments.length > 0) && !isProcessing
 
@@ -102,6 +142,7 @@ function ChatInputInner({
     }
     if (newAttachments.length > 0) {
       setAttachments((prev) => [...prev, ...newAttachments])
+      setFocusNonce((value) => value + 1)
     }
   }, [])
 
@@ -157,27 +198,45 @@ function ChatInputInner({
   return (
     <div className="rounded-lg border border-border bg-background shadow-none">
       {attachments.length > 0 && (
-        <div className="flex flex-wrap gap-1.5 px-4 pb-1 pt-3">
-          {attachments.map((attachment) => (
-            <span
-              key={attachment.id}
-              className="inline-flex items-center gap-1.5 rounded-md bg-muted px-2 py-1 text-xs text-muted-foreground"
-            >
-              {attachment.isImage && attachment.thumbnailUrl ? (
-                <img src={attachment.thumbnailUrl} alt="" className="size-4 rounded object-cover" />
-              ) : (
-                <Paperclip className="size-3" />
-              )}
-              <span className="max-w-[120px] truncate">{attachment.filename}</span>
-              <button
-                type="button"
-                onClick={() => removeAttachment(attachment.id)}
-                className="transition-colors hover:text-foreground"
+        <div className="flex flex-wrap gap-2 px-4 pb-1 pt-3">
+          {attachments.map((attachment) => {
+            const attachmentType = getAttachmentTypeLabel(attachment)
+            const attachmentName = getAttachmentDisplayName(attachment)
+            const Icon = getAttachmentIcon(getAttachmentIconKind(attachment))
+
+            return (
+              <span
+                key={attachment.id}
+                className="group relative inline-flex min-w-[230px] max-w-[320px] items-center gap-2 rounded-xl border border-border/50 bg-muted/80 px-2.5 py-2"
               >
-                <X className="size-3" />
-              </button>
-            </span>
-          ))}
+                <span
+                  className={cn(
+                    'flex size-9 shrink-0 items-center justify-center overflow-hidden rounded-lg',
+                    attachment.isImage && attachment.thumbnailUrl
+                      ? 'bg-muted'
+                      : getAttachmentToneClass(attachmentType)
+                  )}
+                >
+                  {attachment.isImage && attachment.thumbnailUrl ? (
+                    <img src={attachment.thumbnailUrl} alt="" className="size-full object-cover" />
+                  ) : (
+                    <Icon className="size-5" />
+                  )}
+                </span>
+                <span className="min-w-0 flex-1">
+                  <span className="block truncate text-sm leading-tight font-medium">{attachmentName}</span>
+                  <span className="block pt-0.5 text-xs leading-tight text-muted-foreground">{attachmentType}</span>
+                </span>
+                <button
+                  type="button"
+                  onClick={() => removeAttachment(attachment.id)}
+                  className="absolute right-1 top-1 flex size-5 items-center justify-center rounded-full border border-border/70 bg-background/70 text-muted-foreground opacity-0 transition-[opacity,color] duration-150 hover:text-foreground group-hover:opacity-100 focus-visible:opacity-100"
+                >
+                  <X className="size-3.5" />
+                </button>
+              </span>
+            )
+          })}
         </div>
       )}
       <div className="flex items-center gap-2 px-4 py-4">
@@ -210,7 +269,7 @@ function ChatInputInner({
           placeholder="Type your message..."
           onKeyDown={handleKeyDown}
           autoFocus={isActive}
-          focusTrigger={isActive ? runId : undefined}
+          focusTrigger={isActive ? `${runId ?? 'new'}:${focusNonce}` : undefined}
           className="min-h-6 rounded-none border-0 py-0 shadow-none focus-visible:ring-0"
         />
         {isProcessing ? (
diff --git a/apps/x/apps/renderer/src/components/chat-message-attachments.tsx b/apps/x/apps/renderer/src/components/chat-message-attachments.tsx
new file mode 100644
index 00000000..40747045
--- /dev/null
+++ b/apps/x/apps/renderer/src/components/chat-message-attachments.tsx
@@ -0,0 +1,137 @@
+import {
+  AudioLines,
+  FileArchive,
+  FileCode2,
+  FileIcon,
+  FileSpreadsheet,
+  FileText,
+  FileVideo,
+} from 'lucide-react'
+import { useEffect, useMemo, useState } from 'react'
+
+import type { MessageAttachment } from '@/lib/chat-conversation'
+import {
+  type AttachmentIconKind,
+  getAttachmentDisplayName,
+  getAttachmentIconKind,
+  getAttachmentToneClass,
+  getAttachmentTypeLabel,
+} from '@/lib/attachment-presentation'
+import { isImageMime, toFileUrl } from '@/lib/file-utils'
+import { cn } from '@/lib/utils'
+
+function getAttachmentIcon(kind: AttachmentIconKind) {
+  switch (kind) {
+    case 'audio':
+      return AudioLines
+    case 'video':
+      return FileVideo
+    case 'spreadsheet':
+      return FileSpreadsheet
+    case 'archive':
+      return FileArchive
+    case 'code':
+      return FileCode2
+    case 'text':
+      return FileText
+    default:
+      return FileIcon
+  }
+}
+
+function ImageAttachmentPreview({ attachment }: { attachment: MessageAttachment }) {
+  const fallbackFileUrl = useMemo(() => toFileUrl(attachment.path), [attachment.path])
+  const [src, setSrc] = useState(attachment.thumbnailUrl || fallbackFileUrl)
+  const [triedBase64, setTriedBase64] = useState(Boolean(attachment.thumbnailUrl))
+
+  useEffect(() => {
+    const nextSrc = attachment.thumbnailUrl || fallbackFileUrl
+    setSrc(nextSrc)
+    setTriedBase64(Boolean(attachment.thumbnailUrl))
+  }, [attachment.thumbnailUrl, fallbackFileUrl])
+
+  const loadBase64 = useMemo(
+    () => async () => {
+      try {
+        const result = await window.ipc.invoke('shell:readFileBase64', { path: attachment.path })
+        const mimeType = result.mimeType || attachment.mediaType || 'image/*'
+        setSrc(`data:${mimeType};base64,${result.data}`)
+      } catch {
+        // Keep current src; fallback rendering (broken image icon) is better than crashing.
+      }
+    },
+    [attachment.mediaType, attachment.path]
+  )
+
+  useEffect(() => {
+    if (attachment.thumbnailUrl || triedBase64) return
+    setTriedBase64(true)
+    void loadBase64()
+  }, [attachment.thumbnailUrl, loadBase64, triedBase64])
+
+  return (
+    <img
+      src={src}
+      alt="Image attachment"
+      className="h-44 w-auto max-w-[300px] rounded-2xl border border-border/70 bg-muted object-cover"
+      onError={() => {
+        if (triedBase64) return
+        setTriedBase64(true)
+        void loadBase64()
+      }}
+    />
+  )
+}
+
+interface ChatMessageAttachmentsProps {
+  attachments: MessageAttachment[]
+  className?: string
+}
+
+export function ChatMessageAttachments({ attachments, className }: ChatMessageAttachmentsProps) {
+  if (attachments.length === 0) return null
+
+  const imageAttachments = attachments.filter((attachment) => isImageMime(attachment.mediaType))
+  const fileAttachments = attachments.filter((attachment) => !isImageMime(attachment.mediaType))
+
+  return (
+    <div className={cn('flex flex-col items-end gap-2', className)}>
+      {imageAttachments.length > 0 && (
+        <div className="flex flex-wrap justify-end gap-2">
+          {imageAttachments.map((attachment, index) => (
+            <ImageAttachmentPreview key={`${attachment.path}-${index}`} attachment={attachment} />
+          ))}
+        </div>
+      )}
+      {fileAttachments.length > 0 && (
+        <div className="flex flex-wrap justify-end gap-2">
+          {fileAttachments.map((attachment, index) => {
+            const Icon = getAttachmentIcon(getAttachmentIconKind(attachment))
+            const attachmentName = getAttachmentDisplayName(attachment)
+            const attachmentType = getAttachmentTypeLabel(attachment)
+            return (
+              <span
+                key={`${attachment.path}-${index}`}
+                className="inline-flex min-w-[240px] max-w-[440px] items-center gap-3 rounded-2xl border border-border/50 bg-muted/75 px-3 py-2.5 text-sm text-foreground"
+                title={attachmentName}
+              >
+                <span
+                  className={cn(
+                    'flex size-12 shrink-0 items-center justify-center rounded-xl',
+                    getAttachmentToneClass(attachmentType)
+                  )}
+                >
+                  <Icon className="size-6 shrink-0" />
+                </span>
+                <span className="min-w-0 flex-1">
+                  <span className="block truncate text-sm leading-tight font-medium">{attachmentName}</span>
+                  <span className="block pt-0.5 text-xs leading-tight text-muted-foreground">{attachmentType}</span>
+                </span>
+              </span>
+            )
+          })}
+        </div>
+      )}
+    </div>
+  )
+}
diff --git a/apps/x/apps/renderer/src/components/chat-sidebar.tsx b/apps/x/apps/renderer/src/components/chat-sidebar.tsx
index a6216deb..f020cdae 100644
--- a/apps/x/apps/renderer/src/components/chat-sidebar.tsx
+++ b/apps/x/apps/renderer/src/components/chat-sidebar.tsx
@@ -1,10 +1,9 @@
 import React, { useCallback, useEffect, useMemo, useRef, useState } from 'react'
-import { Maximize2, Minimize2, Paperclip, SquarePen } from 'lucide-react'
+import { Maximize2, Minimize2, SquarePen } from 'lucide-react'
 
 import { Button } from '@/components/ui/button'
 import { cn } from '@/lib/utils'
 import { Tooltip, TooltipContent, TooltipTrigger } from '@/components/ui/tooltip'
-import { isImageMime } from '@/lib/file-utils'
 import {
   Conversation,
   ConversationContent,
@@ -27,6 +26,7 @@ import { FileCardProvider } from '@/contexts/file-card-context'
 import { MarkdownPreOverride } from '@/components/ai-elements/markdown-code-override'
 import { TabBar, type ChatTab } from '@/components/tab-bar'
 import { ChatInputWithMentions, type StagedAttachment } from '@/components/chat-input-with-mentions'
+import { ChatMessageAttachments } from '@/components/chat-message-attachments'
 import { wikiLabel } from '@/lib/wiki-links'
 import {
   type ChatTabViewState,
@@ -260,24 +260,12 @@ export function ChatSidebar({
         if (item.attachments && item.attachments.length > 0) {
           return (
             <Message key={item.id} from={item.role}>
-              <MessageContent>
-                <div className="mb-2 flex flex-wrap gap-1.5">
-                  {item.attachments.map((attachment, index) => (
-                    <span
-                      key={index}
-                      className="inline-flex items-center gap-1.5 rounded-md bg-muted px-2 py-1 text-xs text-muted-foreground"
-                    >
-                      {isImageMime(attachment.mediaType) ? (
-                        <span className="size-3 rounded bg-primary/20" />
-                      ) : (
-                        <Paperclip className="size-3" />
-                      )}
-                      {attachment.filename}
-                    </span>
-                  ))}
-                </div>
-                {item.content}
+              <MessageContent className="group-[.is-user]:bg-transparent group-[.is-user]:px-0 group-[.is-user]:py-0 group-[.is-user]:rounded-none">
+                <ChatMessageAttachments attachments={item.attachments} />
               </MessageContent>
+              {item.content && (
+                <MessageContent>{item.content}</MessageContent>
+              )}
             </Message>
           )
         }
diff --git a/apps/x/apps/renderer/src/lib/attachment-presentation.ts b/apps/x/apps/renderer/src/lib/attachment-presentation.ts
new file mode 100644
index 00000000..7948cf1a
--- /dev/null
+++ b/apps/x/apps/renderer/src/lib/attachment-presentation.ts
@@ -0,0 +1,107 @@
+import { getExtension } from '@/lib/file-utils'
+
+export type AttachmentLike = {
+  filename?: string
+  path: string
+  mediaType: string
+}
+
+export type AttachmentIconKind =
+  | 'audio'
+  | 'video'
+  | 'spreadsheet'
+  | 'archive'
+  | 'code'
+  | 'text'
+  | 'file'
+
+const ARCHIVE_EXTENSIONS = new Set([
+  'zip', 'rar', '7z', 'tar', 'gz', 'bz2', 'xz',
+])
+
+const SPREADSHEET_EXTENSIONS = new Set([
+  'csv', 'tsv', 'xls', 'xlsx',
+])
+
+const CODE_EXTENSIONS = new Set([
+  'js', 'jsx', 'ts', 'tsx', 'json', 'yaml', 'yml', 'toml', 'xml',
+  'py', 'rb', 'go', 'rs', 'java', 'kt', 'c', 'cpp', 'h', 'hpp',
+  'cs', 'php', 'swift', 'sh', 'sql', 'html', 'css', 'scss', 'md',
+])
+
+export function getAttachmentDisplayName(attachment: AttachmentLike): string {
+  if (attachment.filename) return attachment.filename
+  const fromPath = attachment.path.split(/[\\/]/).pop()
+  return fromPath || attachment.path
+}
+
+export function getAttachmentTypeLabel(attachment: AttachmentLike): string {
+  const ext = getExtension(getAttachmentDisplayName(attachment))
+  if (ext) return ext.toUpperCase()
+
+  const mediaType = attachment.mediaType.toLowerCase()
+  if (mediaType.startsWith('audio/')) return 'AUDIO'
+  if (mediaType.startsWith('video/')) return 'VIDEO'
+  if (mediaType.startsWith('text/')) return 'TEXT'
+  if (mediaType.startsWith('image/')) return 'IMAGE'
+
+  const [, subtypeRaw = 'file'] = mediaType.split('/')
+  const subtype = subtypeRaw.split(';')[0].split('+').pop() || 'file'
+  const cleaned = subtype.replace(/[^a-z0-9]/gi, '')
+  return cleaned ? cleaned.toUpperCase() : 'FILE'
+}
+
+export function getAttachmentIconKind(attachment: AttachmentLike): AttachmentIconKind {
+  const mediaType = attachment.mediaType.toLowerCase()
+  const ext = getExtension(attachment.filename || attachment.path)
+
+  if (mediaType.startsWith('audio/')) return 'audio'
+  if (mediaType.startsWith('video/')) return 'video'
+  if (mediaType.includes('spreadsheet') || SPREADSHEET_EXTENSIONS.has(ext)) return 'spreadsheet'
+  if (mediaType.includes('zip') || mediaType.includes('compressed') || ARCHIVE_EXTENSIONS.has(ext)) return 'archive'
+  if (
+    mediaType.includes('json')
+    || mediaType.includes('javascript')
+    || mediaType.includes('typescript')
+    || mediaType.includes('xml')
+    || CODE_EXTENSIONS.has(ext)
+  ) {
+    return 'code'
+  }
+  if (mediaType.startsWith('text/') || mediaType.includes('pdf') || mediaType.includes('document')) {
+    return 'text'
+  }
+
+  return 'file'
+}
+
+export function getAttachmentToneClass(typeLabel: string): string {
+  switch (typeLabel) {
+    case 'PDF':
+      return 'bg-red-500 text-white'
+    case 'CSV':
+    case 'XLS':
+    case 'XLSX':
+    case 'TSV':
+      return 'bg-emerald-500 text-white'
+    case 'ZIP':
+    case 'RAR':
+    case '7Z':
+    case 'TAR':
+    case 'GZ':
+      return 'bg-amber-500 text-white'
+    case 'MP3':
+    case 'WAV':
+    case 'M4A':
+    case 'FLAC':
+    case 'AAC':
+      return 'bg-fuchsia-500 text-white'
+    case 'MP4':
+    case 'MOV':
+    case 'AVI':
+    case 'WEBM':
+      return 'bg-violet-500 text-white'
+    default:
+      return 'bg-primary/85 text-primary-foreground'
+  }
+}
diff --git a/apps/x/apps/renderer/src/lib/chat-conversation.ts b/apps/x/apps/renderer/src/lib/chat-conversation.ts
index c9623cd6..5d52fcd7 100644
--- a/apps/x/apps/renderer/src/lib/chat-conversation.ts
+++ b/apps/x/apps/renderer/src/lib/chat-conversation.ts
@@ -8,6 +8,7 @@ export interface MessageAttachment {
   filename: string
   mediaType: string
   size?: number
+  thumbnailUrl?: string
 }
 
 export interface ChatMessage {
diff --git a/apps/x/apps/renderer/src/lib/file-utils.ts b/apps/x/apps/renderer/src/lib/file-utils.ts
index bbebbb02..3ac3431a 100644
--- a/apps/x/apps/renderer/src/lib/file-utils.ts
+++ b/apps/x/apps/renderer/src/lib/file-utils.ts
@@ -41,3 +41,21 @@ export function getExtension(filePath: string): string {
     const dotIndex = name.lastIndexOf('.');
     return dotIndex > 0 ? name.slice(dotIndex + 1).toLowerCase() : '';
 }
+
+export function toFileUrl(filePath: string): string {
+    if (!filePath) return filePath;
+    if (
+        filePath.startsWith('data:') ||
+        filePath.startsWith('file://') ||
+        filePath.startsWith('http://') ||
+        filePath.startsWith('https://')
+    ) {
+        return filePath;
+    }
+    const normalized = filePath.replace(/\\/g, '/');
+    const encoded = encodeURI(normalized);
+    if (/^[A-Za-z]:\//.test(normalized)) {
+        return `file:///${encoded}`;
+    }
+    return `file://${encoded}`;
+}