feat(web): improve message UX, voice gestures, and attachments

app/media/repository.py

@@ -1,6 +1,8 @@
+from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.media.models import Attachment
+from app.messages.models import Message
 
 
 async def create_attachment(
@@ -24,3 +26,23 @@ async def create_attachment(
 
 async def get_attachment_by_id(db: AsyncSession, attachment_id: int) -> Attachment | None:
     return await db.get(Attachment, attachment_id)
+
+
+async def list_chat_attachments(
+    db: AsyncSession,
+    *,
+    chat_id: int,
+    limit: int = 100,
+    before_id: int | None = None,
+) -> list[tuple[Attachment, Message]]:
+    stmt = (
+        select(Attachment, Message)
+        .join(Message, Message.id == Attachment.message_id)
+        .where(Message.chat_id == chat_id)
+        .order_by(Attachment.id.desc())
+        .limit(limit)
+    )
+    if before_id is not None:
+        stmt = stmt.where(Attachment.id < before_id)
+    result = await db.execute(stmt)
+    return [(row[0], row[1]) for row in result.all()]

app/media/router.py

@@ -3,8 +3,8 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.auth.service import get_current_user
 from app.database.session import get_db
-from app.media.schemas import AttachmentCreateRequest, AttachmentRead, UploadUrlRequest, UploadUrlResponse
-from app.media.service import generate_upload_url, store_attachment_metadata
+from app.media.schemas import AttachmentCreateRequest, AttachmentRead, ChatAttachmentRead, UploadUrlRequest, UploadUrlResponse
+from app.media.service import generate_upload_url, list_attachments_for_chat, store_attachment_metadata
 from app.users.models import User
 
 router = APIRouter(prefix="/media", tags=["media"])
@@ -25,3 +25,20 @@ async def create_attachment_metadata(
     current_user: User = Depends(get_current_user),
 ) -> AttachmentRead:
     return await store_attachment_metadata(db, user_id=current_user.id, payload=payload)
+
+
+@router.get("/chats/{chat_id}/attachments", response_model=list[ChatAttachmentRead])
+async def list_chat_attachments_endpoint(
+    chat_id: int,
+    limit: int = 100,
+    before_id: int | None = None,
+    db: AsyncSession = Depends(get_db),
+    current_user: User = Depends(get_current_user),
+) -> list[ChatAttachmentRead]:
+    return await list_attachments_for_chat(
+        db,
+        user_id=current_user.id,
+        chat_id=chat_id,
+        limit=limit,
+        before_id=before_id,
+    )

app/media/schemas.py

@@ -1,4 +1,5 @@
 from pydantic import BaseModel, ConfigDict, Field
+from datetime import datetime
 
 
 class UploadUrlRequest(BaseModel):
@@ -30,3 +31,13 @@ class AttachmentRead(BaseModel):
     file_url: str
     file_type: str
     file_size: int
+
+
+class ChatAttachmentRead(BaseModel):
+    id: int
+    message_id: int
+    sender_id: int
+    message_created_at: datetime
+    file_url: str
+    file_type: str
+    file_size: int

app/media/service.py

@@ -10,7 +10,8 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.config.settings import settings
 from app.media import repository
-from app.media.schemas import AttachmentCreateRequest, AttachmentRead, UploadUrlRequest, UploadUrlResponse
+from app.media.schemas import AttachmentCreateRequest, AttachmentRead, ChatAttachmentRead, UploadUrlRequest, UploadUrlResponse
+from app.chats.service import ensure_chat_membership
 from app.messages.repository import get_message_by_id
 
 ALLOWED_MIME_TYPES = {
@@ -134,3 +135,32 @@ async def store_attachment_metadata(
     await db.commit()
     await db.refresh(attachment)
     return AttachmentRead.model_validate(attachment)
+
+
+async def list_attachments_for_chat(
+    db: AsyncSession,
+    *,
+    user_id: int,
+    chat_id: int,
+    limit: int = 100,
+    before_id: int | None = None,
+) -> list[ChatAttachmentRead]:
+    await ensure_chat_membership(db, chat_id=chat_id, user_id=user_id)
+    rows = await repository.list_chat_attachments(
+        db,
+        chat_id=chat_id,
+        limit=max(1, min(limit, 200)),
+        before_id=before_id,
+    )
+    return [
+        ChatAttachmentRead(
+            id=attachment.id,
+            message_id=attachment.message_id,
+            sender_id=message.sender_id,
+            message_created_at=message.created_at,
+            file_url=attachment.file_url,
+            file_type=attachment.file_type,
+            file_size=attachment.file_size,
+        )
+        for attachment, message in rows
+    ]

web/src/api/chats.ts

@@ -1,5 +1,17 @@
 import { http } from "./http";
-import type { Chat, ChatDetail, ChatInviteLink, ChatMember, ChatMemberRole, ChatType, DiscoverChat, Message, MessageReaction, MessageType } from "../chat/types";
+import type {
+  Chat,
+  ChatAttachment,
+  ChatDetail,
+  ChatInviteLink,
+  ChatMember,
+  ChatMemberRole,
+  ChatType,
+  DiscoverChat,
+  Message,
+  MessageReaction,
+  MessageType
+} from "../chat/types";
 import axios from "axios";
 
 export interface ChatNotificationSettings {
@@ -225,6 +237,16 @@ export async function joinByInvite(token: string): Promise<Chat> {
   return data;
 }
 
+export async function getChatAttachments(chatId: number, limit = 100, beforeId?: number): Promise<ChatAttachment[]> {
+  const { data } = await http.get<ChatAttachment[]>(`/media/chats/${chatId}/attachments`, {
+    params: {
+      limit,
+      before_id: beforeId
+    }
+  });
+  return data;
+}
+
 export async function deleteMessage(messageId: number, forAll = false): Promise<void> {
   await http.delete(`/messages/${messageId}`, { params: { for_all: forAll } });
 }

web/src/chat/types.ts

@@ -97,3 +97,13 @@ export interface ChatInviteLink {
   token: string;
   invite_url: string;
 }
+
+export interface ChatAttachment {
+  id: number;
+  message_id: number;
+  sender_id: number;
+  message_created_at: string;
+  file_url: string;
+  file_type: string;
+  file_size: number;
+}

web/src/components/ChatInfoPanel.tsx

@@ -3,6 +3,7 @@ import { createPortal } from "react-dom";
 import {
   addChatMember,
   createInviteLink,
+  getChatAttachments,
   getChatNotificationSettings,
   getChatDetail,
   leaveChat,
@@ -13,7 +14,7 @@ import {
   updateChatTitle
 } from "../api/chats";
 import { blockUser, getUserById, listBlockedUsers, searchUsers, unblockUser } from "../api/users";
-import type { AuthUser, ChatDetail, ChatMember, UserSearchItem } from "../chat/types";
+import type { AuthUser, ChatAttachment, ChatDetail, ChatMember, UserSearchItem } from "../chat/types";
 import { useAuthStore } from "../store/authStore";
 import { useChatStore } from "../store/chatStore";
 
@@ -41,6 +42,9 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
   const [counterpartBlocked, setCounterpartBlocked] = useState(false);
   const [savingBlock, setSavingBlock] = useState(false);
   const [inviteLink, setInviteLink] = useState<string | null>(null);
+  const [attachments, setAttachments] = useState<ChatAttachment[]>([]);
+  const [attachmentsLoading, setAttachmentsLoading] = useState(false);
+  const [attachmentCtx, setAttachmentCtx] = useState<{ x: number; y: number; url: string } | null>(null);
 
   const myRole = useMemo(() => members.find((m) => m.user_id === me?.id)?.role, [members, me?.id]);
   const isGroupLike = chat?.type === "group" || chat?.type === "channel";
@@ -67,6 +71,7 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
     let cancelled = false;
     setLoading(true);
     setError(null);
+    setAttachmentsLoading(true);
     void (async () => {
       try {
         const detail = await getChatDetail(chatId);
@@ -92,10 +97,17 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
           setCounterpartBlocked(false);
         }
         await refreshMembers(chatId);
+        const chatAttachments = await getChatAttachments(chatId, 120);
+        if (!cancelled) {
+          setAttachments(chatAttachments);
+        }
       } catch {
         if (!cancelled) setError("Failed to load chat info");
       } finally {
-        if (!cancelled) setLoading(false);
+        if (!cancelled) {
+          setLoading(false);
+          setAttachmentsLoading(false);
+        }
       }
     })();
     return () => {
@@ -120,7 +132,13 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
   }
 
   return createPortal(
-    <div className="fixed inset-0 z-[120] bg-slate-950/55" onClick={onClose}>
+    <div
+      className="fixed inset-0 z-[120] bg-slate-950/55"
+      onClick={() => {
+        setAttachmentCtx(null);
+        onClose();
+      }}
+    >
       <aside className="absolute right-0 top-0 h-full w-full max-w-sm border-l border-slate-700/70 bg-slate-900/95 p-4 shadow-2xl" onClick={(e) => e.stopPropagation()}>
         <div className="mb-3 flex items-center justify-between">
           <p className="text-sm font-semibold">Chat info</p>
@@ -321,6 +339,65 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
               </div>
             ) : null}
 
+            <div className="mb-3 rounded-lg border border-slate-700/70 bg-slate-800/60 p-3">
+              <p className="mb-2 text-xs font-semibold uppercase tracking-wide text-slate-300">
+                Media & Files {attachments.length > 0 ? `(${attachments.length})` : ""}
+              </p>
+              {attachmentsLoading ? <p className="text-xs text-slate-400">Loading attachments...</p> : null}
+              {!attachmentsLoading && attachments.length === 0 ? <p className="text-xs text-slate-400">No attachments yet</p> : null}
+
+              {!attachmentsLoading ? (
+                <>
+                  <div className="mb-2 grid grid-cols-3 gap-1">
+                    {attachments
+                      .filter((item) => item.file_type.startsWith("image/"))
+                      .slice(0, 9)
+                      .map((item) => (
+                        <button
+                          className="group relative aspect-square overflow-hidden rounded-md border border-slate-700/70 bg-slate-900"
+                          key={`media-image-${item.id}`}
+                          onClick={() => window.open(item.file_url, "_blank", "noopener,noreferrer")}
+                          onContextMenu={(event) => {
+                            event.preventDefault();
+                            setAttachmentCtx({
+                              x: Math.min(event.clientX + 4, window.innerWidth - 190),
+                              y: Math.min(event.clientY + 4, window.innerHeight - 120),
+                              url: item.file_url
+                            });
+                          }}
+                          type="button"
+                        >
+                          <img alt="attachment" className="h-full w-full object-cover transition group-hover:scale-105" src={item.file_url} />
+                        </button>
+                      ))}
+                  </div>
+                  <div className="tg-scrollbar max-h-44 space-y-1 overflow-auto">
+                    {attachments.slice(0, 40).map((item) => (
+                      <button
+                        className="block w-full rounded-md border border-slate-700/60 bg-slate-900/70 px-2 py-1.5 text-left hover:bg-slate-700/70"
+                        key={`media-item-${item.id}`}
+                        onClick={() => window.open(item.file_url, "_blank", "noopener,noreferrer")}
+                        onContextMenu={(event) => {
+                          event.preventDefault();
+                          setAttachmentCtx({
+                            x: Math.min(event.clientX + 4, window.innerWidth - 190),
+                            y: Math.min(event.clientY + 4, window.innerHeight - 120),
+                            url: item.file_url
+                          });
+                        }}
+                        type="button"
+                      >
+                        <p className="truncate text-xs font-semibold text-slate-200">{extractFileName(item.file_url)}</p>
+                        <p className="text-[11px] text-slate-400">
+                          {attachmentKind(item.file_type)} • {formatBytes(item.file_size)}
+                        </p>
+                      </button>
+                    ))}
+                  </div>
+                </>
+              ) : null}
+            </div>
+
             {chat.type === "private" && !chat.is_saved && chat.counterpart_user_id ? (
               <button
                 className="mb-3 w-full rounded bg-slate-700 px-3 py-2 text-sm disabled:opacity-60"
@@ -366,6 +443,34 @@ export function ChatInfoPanel({ chatId, open, onClose }: Props) {
           </>
         ) : null}
       </aside>
+      {attachmentCtx ? (
+        <div
+          className="fixed z-[130] w-44 rounded-lg border border-slate-700/90 bg-slate-900/95 p-1 shadow-2xl"
+          style={{ left: attachmentCtx.x, top: attachmentCtx.y }}
+        >
+          <a className="block rounded px-2 py-1.5 text-sm hover:bg-slate-800" href={attachmentCtx.url} rel="noreferrer" target="_blank">
+            Open
+          </a>
+          <a className="block rounded px-2 py-1.5 text-sm hover:bg-slate-800" href={attachmentCtx.url} download>
+            Download
+          </a>
+          <button
+            className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
+            onClick={async () => {
+              try {
+                await navigator.clipboard.writeText(attachmentCtx.url);
+              } catch {
+                return;
+              } finally {
+                setAttachmentCtx(null);
+              }
+            }}
+            type="button"
+          >
+            Copy link
+          </button>
+        </div>
+      ) : null}
     </div>,
     document.body
   );
@@ -383,3 +488,28 @@ function formatLastSeen(value: string): string {
     minute: "2-digit"
   });
 }
+
+function formatBytes(size: number): string {
+  if (size < 1024) return `${size} B`;
+  if (size < 1024 * 1024) return `${(size / 1024).toFixed(1)} KB`;
+  return `${(size / (1024 * 1024)).toFixed(1)} MB`;
+}
+
+function extractFileName(url: string): string {
+  try {
+    const parsed = new URL(url);
+    const value = parsed.pathname.split("/").pop();
+    return decodeURIComponent(value || "file");
+  } catch {
+    const value = url.split("/").pop();
+    return value ? decodeURIComponent(value) : "file";
+  }
+}
+
+function attachmentKind(fileType: string): string {
+  if (fileType.startsWith("image/")) return "Photo";
+  if (fileType.startsWith("video/")) return "Video";
+  if (fileType.startsWith("audio/")) return "Audio";
+  if (fileType === "application/pdf") return "PDF";
+  return "File";
+}

web/src/components/MessageComposer.tsx

@@ -1,9 +1,11 @@
-import { useEffect, useRef, useState, type KeyboardEvent } from "react";
+import { useEffect, useRef, useState, type KeyboardEvent, type PointerEvent } from "react";
 import { attachFile, requestUploadUrl, sendMessageWithClientId, uploadToPresignedUrl } from "../api/chats";
 import { useAuthStore } from "../store/authStore";
 import { useChatStore } from "../store/chatStore";
 import { buildWsUrl } from "../utils/ws";
 
+type RecordingState = "idle" | "recording" | "locked";
+
 export function MessageComposer() {
   const activeChatId = useChatStore((s) => s.activeChatId);
   const me = useAuthStore((s) => s.me);
@@ -16,17 +18,39 @@ export function MessageComposer() {
   const replyToByChat = useChatStore((s) => s.replyToByChat);
   const setReplyToMessage = useChatStore((s) => s.setReplyToMessage);
   const accessToken = useAuthStore((s) => s.accessToken);
+
   const [text, setText] = useState("");
   const wsRef = useRef<WebSocket | null>(null);
   const recorderRef = useRef<MediaRecorder | null>(null);
+  const recordingStreamRef = useRef<MediaStream | null>(null);
   const chunksRef = useRef<BlobPart[]>([]);
+  const sendVoiceOnStopRef = useRef<boolean>(true);
+  const recordingStartedAtRef = useRef<number | null>(null);
+  const pointerStartYRef = useRef<number>(0);
+  const pointerStartXRef = useRef<number>(0);
+  const pointerCancelArmedRef = useRef<boolean>(false);
+  const pointerMoveHandlerRef = useRef<((event: globalThis.PointerEvent) => void) | null>(null);
+  const pointerUpHandlerRef = useRef<((event: globalThis.PointerEvent) => void) | null>(null);
+  const recordingStateRef = useRef<RecordingState>("idle");
+
   const [isUploading, setIsUploading] = useState(false);
   const [uploadProgress, setUploadProgress] = useState(0);
   const [uploadError, setUploadError] = useState<string | null>(null);
   const [selectedFile, setSelectedFile] = useState<File | null>(null);
   const [selectedType, setSelectedType] = useState<"file" | "image" | "video" | "audio">("file");
   const [previewUrl, setPreviewUrl] = useState<string | null>(null);
-  const [isRecording, setIsRecording] = useState(false);
+  const [showAttachMenu, setShowAttachMenu] = useState(false);
+  const [captionDraft, setCaptionDraft] = useState("");
+  const mediaInputRef = useRef<HTMLInputElement | null>(null);
+  const fileInputRef = useRef<HTMLInputElement | null>(null);
+
+  const [recordingState, setRecordingState] = useState<RecordingState>("idle");
+  const [recordSeconds, setRecordSeconds] = useState(0);
+  const [dragHint, setDragHint] = useState<"idle" | "lock" | "cancel">("idle");
+
+  useEffect(() => {
+    recordingStateRef.current = recordingState;
+  }, [recordingState]);
 
   useEffect(() => {
     if (!activeChatId) {
@@ -46,9 +70,29 @@ export function MessageComposer() {
       if (previewUrl) {
         URL.revokeObjectURL(previewUrl);
       }
+      if (pointerMoveHandlerRef.current) {
+        window.removeEventListener("pointermove", pointerMoveHandlerRef.current);
+      }
+      if (pointerUpHandlerRef.current) {
+        window.removeEventListener("pointerup", pointerUpHandlerRef.current);
+      }
     };
   }, [previewUrl]);
 
+  useEffect(() => {
+    if (recordingState === "idle") {
+      return;
+    }
+    const interval = window.setInterval(() => {
+      if (!recordingStartedAtRef.current) {
+        return;
+      }
+      const sec = Math.max(0, Math.floor((Date.now() - recordingStartedAtRef.current) / 1000));
+      setRecordSeconds(sec);
+    }, 250);
+    return () => window.clearInterval(interval);
+  }, [recordingState]);
+
   function makeClientMessageId(): string {
     if (typeof crypto !== "undefined" && "randomUUID" in crypto) {
       return crypto.randomUUID();
@@ -147,15 +191,9 @@ export function MessageComposer() {
   }
 
   function inferType(file: File): "file" | "image" | "video" | "audio" {
-    if (file.type.startsWith("image/")) {
-      return "image";
-    }
-    if (file.type.startsWith("video/")) {
-      return "video";
-    }
-    if (file.type.startsWith("audio/")) {
-      return "audio";
-    }
+    if (file.type.startsWith("image/")) return "image";
+    if (file.type.startsWith("video/")) return "video";
+    if (file.type.startsWith("audio/")) return "audio";
     return "file";
   }
 
@@ -209,41 +247,136 @@ export function MessageComposer() {
   }
 
   async function startRecord() {
+    if (recordingState !== "idle") {
+      return false;
+    }
     try {
       if (navigator.permissions && navigator.permissions.query) {
         const permission = await navigator.permissions.query({ name: "microphone" as PermissionName });
         if (permission.state === "denied") {
           setUploadError("Microphone access denied. Allow microphone in browser site permissions.");
-          return;
+          return false;
         }
       }
       const stream = await navigator.mediaDevices.getUserMedia({ audio: true });
       const recorder = new MediaRecorder(stream);
+      recordingStreamRef.current = stream;
       chunksRef.current = [];
-      recorder.ondataavailable = (e) => chunksRef.current.push(e.data);
+      sendVoiceOnStopRef.current = true;
+      recorder.ondataavailable = (event) => chunksRef.current.push(event.data);
       recorder.onstop = async () => {
-        const blob = new Blob(chunksRef.current, { type: "audio/webm" });
+        const shouldSend = sendVoiceOnStopRef.current;
+        const data = [...chunksRef.current];
+        chunksRef.current = [];
+        if (recordingStreamRef.current) {
+          recordingStreamRef.current.getTracks().forEach((track) => track.stop());
+          recordingStreamRef.current = null;
+        }
+        if (!shouldSend || data.length === 0) {
+          return;
+        }
+        const blob = new Blob(data, { type: "audio/webm" });
         const file = new File([blob], `voice-${Date.now()}.webm`, { type: "audio/webm" });
-        setIsRecording(false);
         await handleUpload(file, "voice");
       };
       recorderRef.current = recorder;
       recorder.start();
-      setIsRecording(true);
+      recordingStartedAtRef.current = Date.now();
+      setRecordSeconds(0);
+      setRecordingState("recording");
+      return true;
     } catch {
       setUploadError("Microphone access denied. Please allow microphone and retry.");
+      return false;
     }
   }
 
-  function stopRecord() {
-    recorderRef.current?.stop();
+  function stopRecord(send: boolean) {
+    sendVoiceOnStopRef.current = send;
+    pointerCancelArmedRef.current = false;
+    setDragHint("idle");
+    if (recorderRef.current && recorderRef.current.state !== "inactive") {
+      recorderRef.current.stop();
+    }
     recorderRef.current = null;
-    setIsRecording(false);
+    recordingStartedAtRef.current = null;
+    setRecordingState("idle");
+    setRecordSeconds(0);
+  }
+
+  async function onMicPointerDown(event: PointerEvent<HTMLButtonElement>) {
+    event.preventDefault();
+    const started = await startRecord();
+    if (!started) {
+      return;
+    }
+    pointerStartYRef.current = event.clientY;
+    pointerStartXRef.current = event.clientX;
+    pointerCancelArmedRef.current = false;
+    setDragHint("idle");
+
+    if (pointerMoveHandlerRef.current) {
+      window.removeEventListener("pointermove", pointerMoveHandlerRef.current);
+    }
+    if (pointerUpHandlerRef.current) {
+      window.removeEventListener("pointerup", pointerUpHandlerRef.current);
+    }
+
+    const onPointerMove = (moveEvent: globalThis.PointerEvent) => {
+      const current = recordingStateRef.current;
+      if (current === "idle") {
+        return;
+      }
+      const deltaY = pointerStartYRef.current - moveEvent.clientY;
+      const deltaX = pointerStartXRef.current - moveEvent.clientX;
+
+      if (current === "recording" && deltaY > 70) {
+        setRecordingState("locked");
+        setDragHint("idle");
+        return;
+      }
+
+      if (current === "recording") {
+        if (deltaX > 90) {
+          pointerCancelArmedRef.current = true;
+          setDragHint("cancel");
+        } else if (deltaY > 40) {
+          pointerCancelArmedRef.current = false;
+          setDragHint("lock");
+        } else {
+          pointerCancelArmedRef.current = false;
+          setDragHint("idle");
+        }
+      }
+    };
+
+    const onPointerUp = () => {
+      if (pointerMoveHandlerRef.current) {
+        window.removeEventListener("pointermove", pointerMoveHandlerRef.current);
+      }
+      if (pointerUpHandlerRef.current) {
+        window.removeEventListener("pointerup", pointerUpHandlerRef.current);
+      }
+      pointerMoveHandlerRef.current = null;
+      pointerUpHandlerRef.current = null;
+
+      const current = recordingStateRef.current;
+      if (current === "recording") {
+        stopRecord(!pointerCancelArmedRef.current);
+      }
+      setDragHint("idle");
+    };
+
+    pointerMoveHandlerRef.current = onPointerMove;
+    pointerUpHandlerRef.current = onPointerUp;
+    window.addEventListener("pointermove", onPointerMove);
+    window.addEventListener("pointerup", onPointerUp);
   }
 
   function selectFile(file: File) {
     setUploadError(null);
     setSelectedFile(file);
+    setShowAttachMenu(false);
     const fileType = inferType(file);
     setSelectedType(fileType);
     if (previewUrl) {
@@ -262,11 +395,23 @@ export function MessageComposer() {
     }
     const uploadFile = await prepareFileForUpload(selectedFile, selectedType);
     await handleUpload(uploadFile, selectedType);
+    if (captionDraft.trim() && activeChatId && me) {
+      const clientMessageId = makeClientMessageId();
+      const textValue = captionDraft.trim();
+      addOptimisticMessage({ chatId: activeChatId, senderId: me.id, type: "text", text: textValue, clientMessageId });
+      try {
+        const message = await sendMessageWithClientId(activeChatId, textValue, "text", clientMessageId);
+        confirmMessageByClientId(activeChatId, clientMessageId, message);
+      } catch {
+        removeOptimisticMessage(activeChatId, clientMessageId);
+      }
+    }
     if (previewUrl) {
       URL.revokeObjectURL(previewUrl);
     }
     setSelectedFile(null);
     setPreviewUrl(null);
+    setCaptionDraft("");
     setSelectedType("file");
     setUploadProgress(0);
   }
@@ -277,18 +422,15 @@ export function MessageComposer() {
     }
     setSelectedFile(null);
     setPreviewUrl(null);
+    setCaptionDraft("");
     setSelectedType("file");
     setUploadProgress(0);
     setUploadError(null);
   }
 
   function formatBytes(size: number): string {
-    if (size < 1024) {
-      return `${size} B`;
-    }
-    if (size < 1024 * 1024) {
-      return `${(size / 1024).toFixed(1)} KB`;
-    }
+    if (size < 1024) return `${size} B`;
+    if (size < 1024 * 1024) return `${(size / 1024).toFixed(1)} KB`;
     return `${(size / (1024 * 1024)).toFixed(1)} MB`;
   }
 
@@ -305,86 +447,186 @@ export function MessageComposer() {
           </button>
         </div>
       ) : null}
-      <div className="mb-2 flex items-center gap-2">
-        <label className="cursor-pointer rounded-full bg-slate-700/80 px-3 py-2 text-xs font-semibold hover:bg-slate-700">
-          +
+
+      {recordingState !== "idle" ? (
+        <div className="mb-2 rounded-xl border border-slate-700/80 bg-slate-900/95 px-3 py-2 text-xs text-slate-200">
+          <div className="flex items-center justify-between">
+            <span>🎤 Recording {formatDuration(recordSeconds)}</span>
+            {recordingState === "recording" ? (
+              <span className={dragHint === "cancel" ? "text-red-300" : dragHint === "lock" ? "text-sky-300" : "text-slate-400"}>
+                {dragHint === "cancel" ? "Release to cancel" : dragHint === "lock" ? "Release up to lock" : "Slide up to lock, left to cancel"}
+              </span>
+            ) : (
+              <span className="text-sky-300">Locked</span>
+            )}
+          </div>
+          {recordingState === "locked" ? (
+            <div className="mt-2 flex gap-2">
+              <button className="w-full rounded bg-slate-700 px-3 py-1.5" onClick={() => stopRecord(false)} type="button">
+                Cancel
+              </button>
+              <button className="w-full rounded bg-sky-500 px-3 py-1.5 font-semibold text-slate-950" onClick={() => stopRecord(true)} type="button">
+                Send Voice
+              </button>
+            </div>
+          ) : null}
+        </div>
+      ) : null}
+
+      <div className="mb-2 flex items-end gap-2">
+        <div className="relative">
+          <button
+            className="h-[42px] min-w-[42px] rounded-full bg-slate-700/85 px-3 text-sm font-semibold text-slate-200 hover:bg-slate-700 disabled:opacity-60"
+            disabled={isUploading || recordingState !== "idle"}
+            onClick={() => setShowAttachMenu((v) => !v)}
+            type="button"
+          >
+            📎
+          </button>
+          {showAttachMenu ? (
+            <div className="absolute bottom-12 left-0 z-20 w-44 rounded-xl border border-slate-700/80 bg-slate-900/95 p-1.5 shadow-2xl">
+              <button
+                className="block w-full rounded-lg px-3 py-2 text-left text-sm hover:bg-slate-800"
+                onClick={() => mediaInputRef.current?.click()}
+                type="button"
+              >
+                Photo or Video
+              </button>
+              <button
+                className="block w-full rounded-lg px-3 py-2 text-left text-sm hover:bg-slate-800"
+                onClick={() => fileInputRef.current?.click()}
+                type="button"
+              >
+                File
+              </button>
+            </div>
+          ) : null}
           <input
+            ref={mediaInputRef}
             className="hidden"
             type="file"
-            disabled={isUploading}
-            onChange={(e) => {
-              const file = e.target.files?.[0];
+            accept="image/*,video/*"
+            disabled={isUploading || recordingState !== "idle"}
+            onChange={(event) => {
+              const file = event.target.files?.[0];
               if (file) {
                 selectFile(file);
               }
-              e.currentTarget.value = "";
+              event.currentTarget.value = "";
             }}
           />
-        </label>
+          <input
+            ref={fileInputRef}
+            className="hidden"
+            type="file"
+            disabled={isUploading || recordingState !== "idle"}
+            onChange={(event) => {
+              const file = event.target.files?.[0];
+              if (file) {
+                selectFile(file);
+              }
+              event.currentTarget.value = "";
+            }}
+          />
+        </div>
+
         <textarea
-          className="flex-1 resize-none rounded-2xl border border-slate-700/80 bg-slate-800/80 px-4 py-2.5 text-sm outline-none placeholder:text-slate-400 focus:border-sky-500"
+          className="min-h-[42px] max-h-40 flex-1 resize-y rounded-2xl border border-slate-700/80 bg-slate-800/80 px-4 py-2.5 text-sm outline-none placeholder:text-slate-400 focus:border-sky-500"
           placeholder="Write a message..."
           rows={1}
           value={text}
           onKeyDown={onComposerKeyDown}
-          onChange={(e) => {
-            const next = e.target.value;
+          onChange={(event) => {
+            const next = event.target.value;
             setText(next);
             if (activeChatId) {
               setDraft(activeChatId, next);
-            }
-            if (activeChatId) {
               const ws = getWs();
               ws?.send(JSON.stringify({ event: "typing_start", payload: { chat_id: activeChatId } }));
             }
           }}
         />
-        <button className="rounded-full bg-sky-500 px-4 py-2.5 text-sm font-semibold text-slate-950 hover:bg-sky-400" onClick={handleSend}>
+
+        <button
+          className="h-[42px] w-[72px] rounded-full bg-sky-500 px-4 text-sm font-semibold text-slate-950 hover:bg-sky-400 disabled:opacity-60"
+          disabled={recordingState !== "idle"}
+          onClick={handleSend}
+          type="button"
+        >
           Send
         </button>
+
+        <button
+          className={`h-[42px] w-[56px] rounded-full px-3 text-sm font-semibold ${recordingState === "idle" ? "bg-emerald-500 text-slate-950 hover:bg-emerald-400" : "bg-slate-700 text-slate-300"}`}
+          disabled={isUploading}
+          onPointerDown={onMicPointerDown}
+          type="button"
+        >
+          Mic
+        </button>
       </div>
+
       {selectedFile ? (
-        <div className="mb-2 rounded-xl border border-slate-700/80 bg-slate-900/95 p-3 text-sm">
-          <div className="mb-2 font-semibold">Ready to send</div>
-          <div className="mb-1 break-all text-slate-300">{selectedFile.name}</div>
-          <div className="mb-2 text-xs text-slate-400">{formatBytes(selectedFile.size)}</div>
+        <div className="mb-2 rounded-2xl border border-slate-700/80 bg-slate-900/95 p-3 text-sm shadow-xl">
+          <div className="mb-2 flex items-center justify-between">
+            <div>
+              <p className="font-semibold">Send {selectedType === "image" || selectedType === "video" ? "Photo" : "File"}</p>
+              <p className="text-xs text-slate-400">{selectedFile.name} • {formatBytes(selectedFile.size)}</p>
+            </div>
+            <button className="rounded bg-slate-700 px-2 py-1 text-xs" onClick={cancelSelectedFile} type="button">
+              ✕
+            </button>
+          </div>
           {previewUrl && selectedType === "image" ? (
-            <img className="mb-2 max-h-56 rounded object-contain" src={previewUrl} alt={selectedFile.name} />
+            <img className="mb-2 max-h-72 w-full rounded-xl object-contain" src={previewUrl} alt={selectedFile.name} />
           ) : null}
           {previewUrl && selectedType === "video" ? (
-            <video className="mb-2 max-h-56 w-full rounded" src={previewUrl} controls muted />
+            <video className="mb-2 max-h-72 w-full rounded-xl" src={previewUrl} controls muted />
           ) : null}
+          {!previewUrl ? (
+            <div className="mb-2 rounded-lg border border-slate-700/80 bg-slate-800/60 px-3 py-2 text-xs text-slate-300">
+              No preview available
+            </div>
+          ) : null}
+
+          <input
+            className="mb-2 w-full rounded-xl border border-slate-700/80 bg-slate-800/80 px-3 py-2 text-sm outline-none placeholder:text-slate-400 focus:border-sky-500"
+            maxLength={1000}
+            placeholder="Add a caption..."
+            value={captionDraft}
+            onChange={(event) => setCaptionDraft(event.target.value)}
+          />
+
           {isUploading ? (
             <div className="mb-2">
               <div className="mb-1 text-xs text-slate-300">Uploading: {uploadProgress}%</div>
               <div className="h-2 rounded bg-slate-700">
-                <div className="h-2 rounded bg-accent transition-all" style={{ width: `${uploadProgress}%` }} />
+                <div className="h-2 rounded bg-sky-500 transition-all" style={{ width: `${uploadProgress}%` }} />
               </div>
             </div>
           ) : null}
           <div className="flex gap-2">
             <button
-              className="rounded-lg bg-sky-500 px-3 py-1 font-semibold text-slate-950 disabled:opacity-50"
+              className="w-full rounded-xl bg-sky-500 px-3 py-2 font-semibold text-slate-950 disabled:opacity-50"
               onClick={() => void sendSelectedFile()}
               disabled={isUploading}
             >
-              Send media
+              Send
             </button>
-            <button className="rounded-lg bg-slate-700 px-3 py-1 disabled:opacity-50" onClick={cancelSelectedFile} disabled={isUploading}>
+            <button className="w-full rounded-xl bg-slate-700 px-3 py-2 disabled:opacity-50" onClick={cancelSelectedFile} disabled={isUploading}>
               Cancel
             </button>
           </div>
         </div>
       ) : null}
+
       {uploadError ? <div className="mb-2 text-sm text-red-400">{uploadError}</div> : null}
-      <div className="flex items-center gap-2 text-sm">
-        <button className="rounded-lg bg-slate-700/90 px-3 py-1.5 disabled:opacity-50" onClick={startRecord} disabled={isUploading || isRecording}>
-          {isRecording ? "Recording..." : "Record Voice"}
-        </button>
-        <button className="rounded-lg bg-slate-700/90 px-3 py-1.5 disabled:opacity-50" onClick={stopRecord} disabled={!isRecording}>
-          Stop
-        </button>
-      </div>
     </div>
   );
 }
+
+function formatDuration(totalSeconds: number): string {
+  const minutes = Math.floor(totalSeconds / 60);
+  const seconds = totalSeconds % 60;
+  return `${String(minutes).padStart(2, "0")}:${String(seconds).padStart(2, "0")}`;
+}

web/src/components/MessageList.tsx

@@ -1,6 +1,12 @@
-import { useEffect, useMemo, useState } from "react";
+import { useEffect, useMemo, useState, type MouseEvent } from "react";
 import { createPortal } from "react-dom";
-import { deleteMessage, forwardMessageBulk, listMessageReactions, pinMessage, toggleMessageReaction } from "../api/chats";
+import {
+  deleteMessage,
+  forwardMessageBulk,
+  listMessageReactions,
+  pinMessage,
+  toggleMessageReaction
+} from "../api/chats";
 import type { Message, MessageReaction } from "../chat/types";
 import { useAuthStore } from "../store/authStore";
 import { useChatStore } from "../store/chatStore";
@@ -13,6 +19,12 @@ type ContextMenuState = {
   messageId: number;
 } | null;
 
+type AttachmentMenuState = {
+  x: number;
+  y: number;
+  url: string;
+} | null;
+
 type PendingDeleteState = {
   chatId: number;
   messages: Message[];
@@ -20,6 +32,8 @@ type PendingDeleteState = {
   timerId: number;
 } | null;
 
+const QUICK_REACTIONS = ["👍", "❤️", "🔥", "😂", "😮", "😢"];
+
 export function MessageList() {
   const me = useAuthStore((s) => s.me);
   const activeChatId = useChatStore((s) => s.activeChatId);
@@ -36,7 +50,9 @@ export function MessageList() {
   const updateChatPinnedMessage = useChatStore((s) => s.updateChatPinnedMessage);
   const removeMessage = useChatStore((s) => s.removeMessage);
   const restoreMessages = useChatStore((s) => s.restoreMessages);
+
   const [ctx, setCtx] = useState<ContextMenuState>(null);
+  const [attachmentCtx, setAttachmentCtx] = useState<AttachmentMenuState>(null);
   const [forwardMessageId, setForwardMessageId] = useState<number | null>(null);
   const [forwardQuery, setForwardQuery] = useState("");
   const [forwardError, setForwardError] = useState<string | null>(null);
@@ -72,10 +88,7 @@ export function MessageList() {
   const focusedMessageId = activeChatId ? (focusedMessageIdByChat[activeChatId] ?? null) : null;
   const hasMore = Boolean(activeChatId && hasMoreByChat[activeChatId]);
   const isLoadingMore = Boolean(activeChatId && loadingMoreByChat[activeChatId]);
-  const selectedMessages = useMemo(
-    () => messages.filter((m) => selectedIds.has(m.id)),
-    [messages, selectedIds]
-  );
+  const selectedMessages = useMemo(() => messages.filter((m) => selectedIds.has(m.id)), [messages, selectedIds]);
   const canDeleteAllForSelection = useMemo(
     () => selectedMessages.length > 0 && selectedMessages.every((m) => canDeleteForEveryone(m, activeChat, me?.id)),
     [selectedMessages, activeChat, me?.id]
@@ -87,6 +100,7 @@ export function MessageList() {
         return;
       }
       setCtx(null);
+      setAttachmentCtx(null);
       setForwardMessageId(null);
       setForwardSelectedChatIds(new Set());
       setDeleteMessageId(null);
@@ -99,6 +113,7 @@ export function MessageList() {
   useEffect(() => {
     setSelectedIds(new Set());
     setCtx(null);
+    setAttachmentCtx(null);
     setDeleteMessageId(null);
     setForwardMessageId(null);
     setForwardSelectedChatIds(new Set());
@@ -131,6 +146,27 @@ export function MessageList() {
   }
   const chatId = activeChatId;
 
+  async function ensureReactionsLoaded(messageId: number) {
+    if (reactionsByMessage[messageId]) {
+      return;
+    }
+    try {
+      const rows = await listMessageReactions(messageId);
+      setReactionsByMessage((state) => ({ ...state, [messageId]: rows }));
+    } catch {
+      return;
+    }
+  }
+
+  async function handleToggleReaction(messageId: number, emoji: string) {
+    try {
+      const rows = await toggleMessageReaction(messageId, emoji);
+      setReactionsByMessage((state) => ({ ...state, [messageId]: rows }));
+    } catch {
+      return;
+    }
+  }
+
   async function handleForwardSubmit() {
     if (!forwardMessageId) return;
     const targetChatIds = [...forwardSelectedChatIds];
@@ -174,27 +210,6 @@ export function MessageList() {
     }
   }
 
-  async function ensureReactionsLoaded(messageId: number) {
-    if (reactionsByMessage[messageId]) {
-      return;
-    }
-    try {
-      const rows = await listMessageReactions(messageId);
-      setReactionsByMessage((state) => ({ ...state, [messageId]: rows }));
-    } catch {
-      return;
-    }
-  }
-
-  async function handleToggleReaction(messageId: number, emoji: string) {
-    try {
-      const rows = await toggleMessageReaction(messageId, emoji);
-      setReactionsByMessage((state) => ({ ...state, [messageId]: rows }));
-    } catch {
-      return;
-    }
-  }
-
   function toggleSelected(messageId: number) {
     setSelectedIds((prev) => {
       const next = new Set(prev);
@@ -283,7 +298,7 @@ export function MessageList() {
   }
 
   return (
-    <div className="flex h-full flex-col" onClick={() => setCtx(null)}>
+    <div className="flex h-full flex-col" onClick={() => { setCtx(null); setAttachmentCtx(null); }}>
       {activeChat?.pinned_message_id ? (
         <div className="border-b border-slate-700/50 bg-slate-900/60 px-4 py-2 text-xs text-sky-300">
           📌 {messagesMap.get(activeChat.pinned_message_id)?.text || "Pinned message"}
@@ -307,7 +322,8 @@ export function MessageList() {
           </div>
         </div>
       ) : null}
-      <div className="tg-scrollbar flex-1 overflow-auto px-3 py-4 md:px-6">
+
+      <div className="tg-scrollbar flex-1 overflow-auto px-2 py-4 md:px-5">
         {hasMore ? (
           <div className="mb-3 flex justify-center">
             <button
@@ -319,10 +335,13 @@ export function MessageList() {
             </button>
           </div>
         ) : null}
+
         {messages.map((message, messageIndex) => {
           const own = message.sender_id === me?.id;
           const replySource = message.reply_to_message_id ? messagesMap.get(message.reply_to_message_id) : null;
           const isSelected = selectedIds.has(message.id);
+          const messageReactions = reactionsByMessage[message.id] ?? [];
+
           return (
             <div key={`${message.id}-${message.client_message_id ?? ""}`}>
               {unreadBoundaryIndex === messageIndex ? (
@@ -334,143 +353,222 @@ export function MessageList() {
                   <span className="h-px flex-1 bg-slate-700/60" />
                 </div>
               ) : null}
+
               <div className={`mb-2 flex ${own ? "justify-end" : "justify-start"}`}>
-              <div
-                id={`message-${message.id}`}
-                className={`max-w-[86%] rounded-2xl px-3 py-2 shadow-sm md:max-w-[72%] ${
-                  own ? "rounded-br-md bg-sky-500/90 text-slate-950" : "rounded-bl-md border border-slate-700/60 bg-slate-900/80 text-slate-100"
-                } ${isSelected ? "ring-2 ring-sky-400/80" : ""} ${focusedMessageId === message.id ? "ring-2 ring-amber-300" : ""}`}
-                onClick={() => {
-                  if (selectedIds.size > 0) {
-                    toggleSelected(message.id);
-                  }
-                }}
-                onContextMenu={(e) => {
-                  e.preventDefault();
-                  void ensureReactionsLoaded(message.id);
-                  const pos = getSafeContextPosition(e.clientX, e.clientY, 160, 108);
-                  setCtx({ x: pos.x, y: pos.y, messageId: message.id });
-                }}
-              >
-                {selectedIds.size > 0 ? (
-                  <div className={`mb-1 inline-flex h-4 w-4 items-center justify-center rounded-full border text-[10px] ${isSelected ? "border-sky-300 bg-sky-300 text-slate-900" : "border-slate-400 text-slate-300"}`}>
-                    {isSelected ? "✓" : ""}
-                  </div>
-                ) : null}
-                {message.forwarded_from_message_id ? (
-                  <div className={`mb-1 rounded-md border-l-2 px-2 py-1 text-[11px] ${own ? "border-slate-900/60 bg-slate-900/10 text-slate-900/75" : "border-sky-400 bg-slate-800/60 text-sky-300"}`}>
-                    ↪ Forwarded message
-                  </div>
-                ) : null}
-                {replySource ? (
-                  <div className={`mb-1 rounded-md border-l-2 px-2 py-1 text-[11px] ${own ? "border-slate-900/60 bg-slate-900/10 text-slate-900/75" : "border-sky-400 bg-slate-800/60 text-slate-300"}`}>
-                    <p className="truncate font-semibold">{replySource.sender_id === me?.id ? "You" : "Reply"}</p>
-                    <p className="truncate">{replySource.text || "[media]"}</p>
-                  </div>
-                ) : null}
-                {renderContent(message.type, message.text)}
-                <div className="mt-1 flex flex-wrap gap-1">
-                  {["👍", "❤️", "🔥"].map((emoji) => {
-                    const items = reactionsByMessage[message.id] ?? [];
-                    const item = items.find((reaction) => reaction.emoji === emoji);
-                    return (
-                      <button
-                        className={`rounded-full border px-2 py-0.5 text-[11px] ${
-                          item?.reacted ? "border-sky-300 bg-sky-500/30" : "border-slate-500/60 bg-slate-700/40"
-                        }`}
-                        key={`${message.id}-${emoji}`}
-                        onClick={() => void handleToggleReaction(message.id, emoji)}
-                        type="button"
-                      >
-                        {emoji}{item ? ` ${item.count}` : ""}
-                      </button>
-                    );
+                <div
+                  id={`message-${message.id}`}
+                  className={`max-w-[90%] rounded-2xl px-3 py-2.5 shadow-sm md:max-w-[70%] ${
+                    own
+                      ? "rounded-br-md bg-gradient-to-b from-sky-500/95 to-sky-600/90 text-slate-950"
+                      : "rounded-bl-md border border-slate-700/60 bg-slate-900/80 text-slate-100"
+                  } ${isSelected ? "ring-2 ring-sky-400/80" : ""} ${focusedMessageId === message.id ? "ring-2 ring-amber-300" : ""}`}
+                  onClick={() => {
+                    if (selectedIds.size > 0) {
+                      toggleSelected(message.id);
+                    }
+                  }}
+                  onContextMenu={(event) => {
+                    event.preventDefault();
+                    void ensureReactionsLoaded(message.id);
+                    const pos = getSafeContextPosition(event.clientX, event.clientY, 220, 220);
+                    setCtx({ x: pos.x, y: pos.y, messageId: message.id });
+                  }}
+                >
+                  {selectedIds.size > 0 ? (
+                    <div
+                      className={`mb-1 inline-flex h-4 w-4 items-center justify-center rounded-full border text-[10px] ${
+                        isSelected ? "border-sky-300 bg-sky-300 text-slate-900" : "border-slate-400 text-slate-300"
+                      }`}
+                    >
+                      {isSelected ? "✓" : ""}
+                    </div>
+                  ) : null}
+
+                  {message.forwarded_from_message_id ? (
+                    <div
+                      className={`mb-1 rounded-md border-l-2 px-2 py-1 text-[11px] ${
+                        own
+                          ? "border-slate-900/60 bg-slate-900/10 text-slate-900/75"
+                          : "border-sky-400 bg-slate-800/60 text-sky-300"
+                      }`}
+                    >
+                      ↪ Forwarded message
+                    </div>
+                  ) : null}
+
+                  {replySource ? (
+                    <div
+                      className={`mb-1 rounded-md border-l-2 px-2 py-1 text-[11px] ${
+                        own
+                          ? "border-slate-900/60 bg-slate-900/10 text-slate-900/75"
+                          : "border-sky-400 bg-slate-800/60 text-slate-300"
+                      }`}
+                    >
+                      <p className="truncate font-semibold">{replySource.sender_id === me?.id ? "You" : "Reply"}</p>
+                      <p className="truncate">{replySource.text || "[media]"}</p>
+                    </div>
+                  ) : null}
+
+                  {renderMessageContent(message.type, message.text, {
+                    onAttachmentContextMenu: (event, url) => {
+                      event.preventDefault();
+                      const pos = getSafeContextPosition(event.clientX, event.clientY, 180, 110);
+                      setAttachmentCtx({ x: pos.x, y: pos.y, url });
+                    }
                   })}
+
+                  {messageReactions.length > 0 ? (
+                    <div className="mt-2 flex flex-wrap gap-1">
+                      {messageReactions.map((reaction) => (
+                        <span
+                          className={`rounded-full border px-2 py-0.5 text-[11px] ${
+                            reaction.reacted
+                              ? "border-sky-300 bg-sky-500/30"
+                              : own
+                                ? "border-slate-900/30 bg-slate-900/10"
+                                : "border-slate-600/60 bg-slate-800/60"
+                          }`}
+                          key={`${message.id}-${reaction.emoji}`}
+                        >
+                          {reaction.emoji} {reaction.count}
+                        </span>
+                      ))}
+                    </div>
+                  ) : null}
+
+                  <p className={`mt-1 flex items-center justify-end gap-1 text-[11px] ${own ? "text-slate-900/85" : "text-slate-400"}`}>
+                    <span>{formatTime(message.created_at)}</span>
+                    {own ? (
+                      <span className={message.delivery_status === "read" ? "text-cyan-900" : ""}>{renderStatus(message.delivery_status)}</span>
+                    ) : null}
+                  </p>
                 </div>
-                <p className={`mt-1 flex items-center justify-end gap-1 text-[11px] ${own ? "text-slate-900/85" : "text-slate-400"}`}>
-                  <span>{formatTime(message.created_at)}</span>
-                  {own ? <span className={message.delivery_status === "read" ? "text-cyan-900" : ""}>{renderStatus(message.delivery_status)}</span> : null}
-                </p>
-              </div>
               </div>
             </div>
           );
         })}
       </div>
+
       <div className="px-5 pb-2 text-xs text-slate-300/80">{(typingByChat[activeChatId] ?? []).length > 0 ? "typing..." : ""}</div>
 
       {ctx
         ? createPortal(
-          <div
-            className="fixed z-[100] w-40 rounded-lg border border-slate-700/80 bg-slate-900/95 p-1 shadow-2xl"
-            style={{ left: ctx.x, top: ctx.y }}
-            onClick={(e) => e.stopPropagation()}
-          >
-            <button
-              className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
-              onClick={() => {
-                const msg = messagesMap.get(ctx.messageId);
-                if (msg) {
-                  setReplyToMessage(chatId, msg);
-                }
-                setCtx(null);
-              }}
+            <div
+              className="fixed z-[110] w-56 rounded-xl border border-slate-700/90 bg-slate-900/95 p-1.5 shadow-2xl"
+              style={{ left: ctx.x, top: ctx.y }}
+              onClick={(event) => event.stopPropagation()}
             >
-              Reply
-            </button>
-            <button
-              className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
-              onClick={() => {
-                setForwardMessageId(ctx.messageId);
-                setForwardQuery("");
-                setForwardError(null);
-                setForwardSelectedChatIds(new Set());
-                setCtx(null);
-              }}
+              <div className="mb-1 flex flex-wrap gap-1 rounded-lg bg-slate-800/80 p-1">
+                {QUICK_REACTIONS.map((emoji) => (
+                  <button
+                    className="rounded-md px-1.5 py-1 text-sm hover:bg-slate-700"
+                    key={emoji}
+                    onClick={() => void handleToggleReaction(ctx.messageId, emoji)}
+                    type="button"
+                  >
+                    {emoji}
+                  </button>
+                ))}
+              </div>
+
+              <button
+                className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
+                onClick={() => {
+                  const msg = messagesMap.get(ctx.messageId);
+                  if (msg) {
+                    setReplyToMessage(chatId, msg);
+                  }
+                  setCtx(null);
+                }}
+              >
+                Reply
+              </button>
+              <button
+                className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
+                onClick={() => {
+                  setForwardMessageId(ctx.messageId);
+                  setForwardQuery("");
+                  setForwardError(null);
+                  setForwardSelectedChatIds(new Set());
+                  setCtx(null);
+                }}
+              >
+                Forward
+              </button>
+              <button
+                className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
+                onClick={() => {
+                  setSelectedIds(new Set([ctx.messageId]));
+                  setCtx(null);
+                }}
+              >
+                Select
+              </button>
+              <button
+                className="block w-full rounded px-2 py-1.5 text-left text-sm text-red-300 hover:bg-slate-800"
+                onClick={() => {
+                  setDeleteMessageId(ctx.messageId);
+                  setDeleteError(null);
+                  setCtx(null);
+                }}
+              >
+                Delete
+              </button>
+              <button className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800" onClick={() => void handlePin(ctx.messageId)}>
+                Pin / Unpin
+              </button>
+            </div>,
+            document.body
+          )
+        : null}
+
+      {attachmentCtx
+        ? createPortal(
+            <div
+              className="fixed z-[111] w-44 rounded-lg border border-slate-700/80 bg-slate-900/95 p-1 shadow-2xl"
+              style={{ left: attachmentCtx.x, top: attachmentCtx.y }}
+              onClick={(event) => event.stopPropagation()}
             >
-              Forward
-            </button>
-            <button
-              className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
-              onClick={() => {
-                setSelectedIds(new Set([ctx.messageId]));
-                setCtx(null);
-              }}
-            >
-              Select
-            </button>
-            <button
-              className="block w-full rounded px-2 py-1.5 text-left text-sm text-red-300 hover:bg-slate-800"
-              onClick={() => {
-                setDeleteMessageId(ctx.messageId);
-                setDeleteError(null);
-                setCtx(null);
-              }}
-            >
-              Delete
-            </button>
-            <button className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800" onClick={() => void handlePin(ctx.messageId)}>
-              Pin / Unpin
-            </button>
-          </div>,
-          document.body
-        )
+              <a className="block rounded px-2 py-1.5 text-sm hover:bg-slate-800" href={attachmentCtx.url} rel="noreferrer" target="_blank">
+                Open
+              </a>
+              <a className="block rounded px-2 py-1.5 text-sm hover:bg-slate-800" href={attachmentCtx.url} download>
+                Download
+              </a>
+              <button
+                className="block w-full rounded px-2 py-1.5 text-left text-sm hover:bg-slate-800"
+                onClick={async () => {
+                  try {
+                    await navigator.clipboard.writeText(attachmentCtx.url);
+                  } catch {
+                    return;
+                  }
+                }}
+                type="button"
+              >
+                Copy link
+              </button>
+            </div>,
+            document.body
+          )
         : null}
 
       {forwardMessageId ? (
         <div className="absolute inset-0 z-50 flex items-end justify-center bg-slate-950/55 p-3" onClick={() => setForwardMessageId(null)}>
-          <div className="w-full rounded-xl border border-slate-700/80 bg-slate-900 p-3" onClick={(e) => e.stopPropagation()}>
+          <div className="w-full rounded-xl border border-slate-700/80 bg-slate-900 p-3" onClick={(event) => event.stopPropagation()}>
             <p className="mb-2 text-sm font-semibold">Forward message</p>
             <input
               className="mb-2 w-full rounded-lg border border-slate-700/80 bg-slate-800/80 px-3 py-2 text-sm outline-none placeholder:text-slate-400 focus:border-sky-500"
               placeholder="Search chats"
               value={forwardQuery}
-              onChange={(e) => setForwardQuery(e.target.value)}
+              onChange={(event) => setForwardQuery(event.target.value)}
             />
             <div className="tg-scrollbar max-h-56 space-y-1 overflow-auto">
               {forwardTargets.map((chat) => (
                 <button
-                  className={`block w-full rounded-lg px-3 py-2 text-left text-sm disabled:opacity-60 ${forwardSelectedChatIds.has(chat.id) ? "bg-sky-500/30" : "bg-slate-800 hover:bg-slate-700"}`}
+                  className={`block w-full rounded-lg px-3 py-2 text-left text-sm disabled:opacity-60 ${
+                    forwardSelectedChatIds.has(chat.id) ? "bg-sky-500/30" : "bg-slate-800 hover:bg-slate-700"
+                  }`}
                   disabled={isForwarding}
                   key={chat.id}
                   onClick={() => {
@@ -506,7 +604,7 @@ export function MessageList() {
 
       {deleteMessageId ? (
         <div className="absolute inset-0 z-50 flex items-end justify-center bg-slate-950/55 p-3" onClick={() => setDeleteMessageId(null)}>
-          <div className="w-full rounded-xl border border-slate-700/80 bg-slate-900 p-3" onClick={(e) => e.stopPropagation()}>
+          <div className="w-full rounded-xl border border-slate-700/80 bg-slate-900 p-3" onClick={(event) => event.stopPropagation()}>
             <p className="mb-2 text-sm font-semibold">Delete message</p>
             <p className="mb-3 text-xs text-slate-400">Choose how to delete this message.</p>
             <div className="space-y-2">
@@ -544,18 +642,70 @@ export function MessageList() {
   );
 }
 
-function renderContent(messageType: string, text: string | null) {
+function renderMessageContent(
+  messageType: string,
+  text: string | null,
+  opts: { onAttachmentContextMenu: (event: MouseEvent<HTMLElement>, url: string) => void }
+) {
   if (!text) return <p className="opacity-80">[empty]</p>;
-  if (messageType === "image") return <img alt="attachment" className="max-h-72 rounded-lg object-cover" src={text} />;
-  if (messageType === "video" || messageType === "circle_video") return <video className="max-h-72 rounded-lg" controls src={text} />;
-  if (messageType === "audio" || messageType === "voice") return <audio controls src={text} />;
-  if (messageType === "file") {
+
+  if (messageType === "image") {
     return (
-      <a className="underline" href={text} rel="noreferrer" target="_blank">
-        Open file
-      </a>
+      <div className="overflow-hidden rounded-xl bg-slate-950/30" onContextMenu={(event) => opts.onAttachmentContextMenu(event, text)}>
+        <img alt="attachment" className="max-h-80 rounded-xl object-cover" draggable={false} src={text} />
+      </div>
     );
   }
+
+  if (messageType === "video" || messageType === "circle_video") {
+    return (
+      <div className="overflow-hidden rounded-xl bg-slate-950/30" onContextMenu={(event) => opts.onAttachmentContextMenu(event, text)}>
+        <video className="max-h-80 rounded-xl" controls src={text} />
+      </div>
+    );
+  }
+
+  if (messageType === "voice") {
+    return (
+      <div className="rounded-xl border border-slate-700/60 bg-slate-950/30 p-2" onContextMenu={(event) => opts.onAttachmentContextMenu(event, text)}>
+        <div className="mb-1 flex items-center gap-2 text-xs text-slate-300">
+          <span className="inline-flex h-7 w-7 items-center justify-center rounded-full bg-slate-700/80">🎤</span>
+          <span className="font-semibold">Voice message</span>
+        </div>
+        <audio className="w-full" controls preload="metadata" src={text} />
+      </div>
+    );
+  }
+
+  if (messageType === "audio") {
+    return (
+      <div className="rounded-xl border border-slate-700/60 bg-slate-950/30 p-2" onContextMenu={(event) => opts.onAttachmentContextMenu(event, text)}>
+        <div className="mb-1 flex items-center gap-2 text-xs text-slate-300">
+          <span className="inline-flex h-7 w-7 items-center justify-center rounded-full bg-slate-700/80">🎵</span>
+          <div className="min-w-0">
+            <p className="truncate font-semibold text-slate-200">{extractFileName(text)}</p>
+            <p className="text-[11px] text-slate-400">Audio file</p>
+          </div>
+        </div>
+        <audio className="w-full" controls preload="metadata" src={text} />
+      </div>
+    );
+  }
+
+  if (messageType === "file") {
+    return (
+        <button
+          className="w-full rounded-xl border border-slate-600/60 bg-slate-800/70 px-3 py-2 text-left"
+          onContextMenu={(event) => opts.onAttachmentContextMenu(event, text)}
+          onClick={() => window.open(text, "_blank", "noopener,noreferrer")}
+          type="button"
+        >
+          <p className="text-xs uppercase tracking-wide text-slate-400">Document</p>
+          <p className="truncate text-sm font-semibold text-slate-100">{extractFileName(text)}</p>
+        </button>
+      );
+  }
+
   return <p className="whitespace-pre-wrap break-words" dangerouslySetInnerHTML={{ __html: formatMessageHtml(text) }} />;
 }
 
@@ -595,3 +745,14 @@ function canDeleteForEveryone(
   if (chat.type === "private") return true;
   return message.sender_id === meId;
 }
+
+function extractFileName(url: string): string {
+  try {
+    const parsed = new URL(url);
+    const value = parsed.pathname.split("/").pop();
+    return decodeURIComponent(value || "file");
+  } catch {
+    const value = url.split("/").pop();
+    return value ? decodeURIComponent(value) : "file";
+  }
+}