fix(logging): redact PII from media-error console warnings

msgContent media load/thumbnail failures now log only the error name+message,
not the full error/event object that may carry content data.

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

src/app/components/emoji-board/EmojiBoard.tsx

@@ -178,6 +178,16 @@ function EmojiSidebar({ activeGroupAtom, packs, onScrollToGroup }: EmojiSidebarP
   const labels = useEmojiGroupLabels();
   const icons = useEmojiGroupIcons();
 
+  const packLabels = useMemo(() => {
+    const map = new Map<string, string | undefined>();
+    packs.forEach((pack) => {
+      let label = pack.meta.name;
+      if (!label) label = isUserId(pack.id) ? 'Personal Pack' : mx.getRoom(pack.id)?.name;
+      map.set(pack.id, label);
+    });
+    return map;
+  }, [mx, packs]);
+
   const handleScrollToGroup = (groupId: string) => {
     setActiveGroupId(groupId);
     onScrollToGroup(groupId);
@@ -198,8 +208,7 @@ function EmojiSidebar({ activeGroupAtom, packs, onScrollToGroup }: EmojiSidebarP
         <SidebarStack>
           <SidebarDivider />
           {packs.map((pack) => {
-            let label = pack.meta.name;
+            const label = packLabels.get(pack.id);
-            if (!label) label = isUserId(pack.id) ? 'Personal Pack' : mx.getRoom(pack.id)?.name;
 
             const url =
               mxcUrlToHttp(mx, pack.getAvatarUrl(usage) ?? '', useAuthentication) ?? undefined;
@@ -252,6 +261,16 @@ function StickerSidebar({ activeGroupAtom, packs, onScrollToGroup }: StickerSide
   const [activeGroupId, setActiveGroupId] = useAtom(activeGroupAtom);
   const usage = ImageUsage.Sticker;
 
+  const packLabels = useMemo(() => {
+    const map = new Map<string, string | undefined>();
+    packs.forEach((pack) => {
+      let label = pack.meta.name;
+      if (!label) label = isUserId(pack.id) ? 'Personal Pack' : mx.getRoom(pack.id)?.name;
+      map.set(pack.id, label);
+    });
+    return map;
+  }, [mx, packs]);
+
   const handleScrollToGroup = (groupId: string) => {
     setActiveGroupId(groupId);
     onScrollToGroup(groupId);
@@ -261,8 +280,7 @@ function StickerSidebar({ activeGroupAtom, packs, onScrollToGroup }: StickerSide
     <Sidebar>
       <SidebarStack>
         {packs.map((pack) => {
-          let label = pack.meta.name;
+          const label = packLabels.get(pack.id);
-          if (!label) label = isUserId(pack.id) ? 'Personal Pack' : mx.getRoom(pack.id)?.name;
 
           const url =
             mxcUrlToHttp(mx, pack.getAvatarUrl(usage) ?? '', useAuthentication) ?? undefined;

src/app/features/call/CallMemberCard.tsx

@@ -9,6 +9,7 @@ import { getMemberAvatarMxc, getMemberDisplayName } from '../../utils/room';
 import { useRoom } from '../../hooks/useRoom';
 import { getMxIdLocalPart, mxcUrlToHttp } from '../../utils/matrix';
 import { UserAvatar } from '../../components/user-avatar';
+import { AvatarDecoration } from '../../components/avatar-decoration/AvatarDecoration';
 import { getMouseEventCords } from '../../utils/dom';
 import * as css from './styles.css';
 
@@ -51,6 +52,7 @@ export function CallMemberCard({ member }: CallMemberCardProps) {
       }
     >
       <Box grow="Yes" gap="300" alignItems="Center">
+        <AvatarDecoration userId={userId}>
           <Avatar size="200" radii="400">
             <UserAvatar
               userId={userId}
@@ -59,6 +61,7 @@ export function CallMemberCard({ member }: CallMemberCardProps) {
               renderFallback={() => <Icon size="50" src={Icons.User} filled />}
             />
           </Avatar>
+        </AvatarDecoration>
         <Box grow="Yes">
           <Text size="L400" truncate>
             {name}

src/app/features/call/CallView.tsx

@@ -1,6 +1,13 @@
 import React, { RefObject, useRef } from 'react';
-import { Badge, Box, color, Header, Scroll, Text, toRem } from 'folds';
+import { useSetAtom } from 'jotai';
-import { useCallEmbed, useCallJoined, useCallEmbedPlacementSync } from '../../hooks/useCallEmbed';
+import { Badge, Box, Button, color, Header, Icon, Icons, Scroll, Text, toRem } from 'folds';
+import {
+  useCallEmbed,
+  useCallJoined,
+  useCallEmbedPlacementSync,
+  useCallLoadError,
+} from '../../hooks/useCallEmbed';
+import { callEmbedAtom } from '../../state/callEmbed';
 import { ContainerColor } from '../../styles/ContainerColor.css';
 import { PrescreenControls } from './PrescreenControls';
 import { usePowerLevelsContext } from '../../hooks/usePowerLevels';
@@ -153,6 +160,37 @@ function CallPrescreen() {
   );
 }
 
+function CallLoadErrorMessage() {
+  const setCallEmbed = useSetAtom(callEmbedAtom);
+
+  // Disposing the embed tears down the hung iframe and returns the user to the
+  // prescreen, from which they can join again ("Retry") or simply walk away.
+  const dismiss = () => setCallEmbed(undefined);
+
+  return (
+    <Box
+      className={css.CallViewContent}
+      direction="Column"
+      alignItems="Center"
+      justifyContent="Center"
+      gap="300"
+    >
+      <Icon src={Icons.Warning} size="400" style={{ color: color.Critical.Main }} />
+      <Text style={{ color: color.Critical.Main }} size="L400" align="Center">
+        The call failed to load. Check your connection and try again.
+      </Text>
+      <Box gap="200" alignItems="Center">
+        <Button variant="Primary" size="300" radii="400" onClick={dismiss}>
+          <Text size="B400">Retry</Text>
+        </Button>
+        <Button variant="Secondary" fill="Soft" size="300" radii="400" onClick={dismiss}>
+          <Text size="B400">Leave</Text>
+        </Button>
+      </Box>
+    </Box>
+  );
+}
+
 type CallJoinedProps = {
   containerRef: RefObject<HTMLDivElement>;
   joined: boolean;
@@ -175,8 +213,13 @@ export function CallView() {
 
   const callEmbed = useCallEmbed();
   const callJoined = useCallJoined(callEmbed);
+  const loadError = useCallLoadError(callEmbed);
 
-  const currentJoined = callEmbed?.roomId === room.roomId && callJoined;
+  const isCurrentRoom = callEmbed?.roomId === room.roomId;
+  const currentJoined = isCurrentRoom && callJoined;
+  // Show the recovery UI when this room's embed failed to load and we never
+  // made it into the call (a hung iframe / blank spinner otherwise).
+  const showLoadError = isCurrentRoom && !currentJoined && Boolean(loadError);
 
   return (
     <Box
@@ -184,8 +227,9 @@ export function CallView() {
       style={{ minWidth: toRem(280) }}
       grow="Yes"
     >
-      {!currentJoined && <CallPrescreen />}
+      {showLoadError && <CallLoadErrorMessage />}
-      <CallJoined joined={currentJoined} containerRef={callContainerRef} />
+      {!currentJoined && !showLoadError && <CallPrescreen />}
+      {!showLoadError && <CallJoined joined={currentJoined} containerRef={callContainerRef} />}
     </Box>
   );
 }

src/app/features/room/RoomInput.tsx

@@ -221,7 +221,7 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
     const showSchedule = composerToolbarButtons?.showSchedule ?? true;
     const [locating, setLocating] = React.useState(false);
     const [locationError, setLocationError] = React.useState<string | null>(null);
-    const handleShareLocation = () => {
+    const handleShareLocation = useCallback(() => {
       if (!navigator.geolocation) {
         setLocationError('Geolocation not supported.');
         setTimeout(() => setLocationError(null), 4000);
@@ -252,7 +252,7 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
         },
         { timeout: 10000 },
       );
-    };
+    }, [mx, roomId]);
 
     const handleVoiceSend = useCallback(
       async (blob: Blob, mimeType: string, durationMs: number, waveform: number[]) => {
@@ -405,16 +405,20 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
       [setSelectedFiles, selectedFiles],
     );
 
-    const handleCancelUpload = (uploads: Upload[]) => {
+    const handleCancelUpload = useCallback(
+      (uploads: Upload[]) => {
         uploads.forEach((upload) => {
           if (upload.status === UploadStatus.Loading) {
             mx.cancelUpload(upload.promise);
           }
         });
         handleRemoveUpload(uploads.map((upload) => upload.file));
-    };
+      },
+      [mx, handleRemoveUpload],
+    );
 
-    const handleSendUpload = async (uploads: UploadSuccess[]) => {
+    const handleSendUpload = useCallback(
+      async (uploads: UploadSuccess[]) => {
         const contentsPromises = uploads.map(async (upload) => {
           const fileItem = selectedFiles.find((f) => f.file === upload.file);
           if (!fileItem) throw new Error('Broken upload');
@@ -469,7 +473,9 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
         handleCancelUpload(uploads);
         const contents = fulfilledPromiseSettledResult(await Promise.allSettled(contentsPromises));
         contents.forEach((content) => mx.sendMessage(roomId, content as any));
-    };
+      },
+      [mx, roomId, selectedFiles, handleCancelUpload],
+    );
 
     const submit = useCallback(() => {
       uploadBoardHandlers.current?.handleSend();
@@ -675,10 +681,13 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
       ReactEditor.focus(editor);
     }, [editor]);
 
-    const handleEmoticonSelect = (key: string, shortcode: string) => {
+    const handleEmoticonSelect = useCallback(
+      (key: string, shortcode: string) => {
         editor.insertNode(createEmoticonElement(key, shortcode));
         moveCursor(editor);
-    };
+      },
+      [editor],
+    );
 
     const handleGifSelect = useCallback(
       async (gifUrl: string, w: number, h: number) => {
@@ -736,7 +745,8 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
       [mx, roomId, alive],
     );
 
-    const handleStickerSelect = async (mxc: string, shortcode: string, label: string) => {
+    const handleStickerSelect = useCallback(
+      async (mxc: string, shortcode: string, label: string) => {
         const stickerUrl = mxcUrlToHttp(mx, mxc, useAuthentication);
         if (!stickerUrl) return;
 
@@ -750,7 +760,9 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
           url: mxc,
           info,
         });
-    };
+      },
+      [mx, roomId, useAuthentication],
+    );
 
     if (room.getType() === 'm.server_notice') {
       return (

src/app/features/room/RoomTimeline.tsx

@@ -906,25 +906,25 @@ export function RoomTimeline({ room, eventId, roomInputRef, editor }: RoomTimeli
     }
   }, [scrollToElement, editId]);
 
-  const handleJumpToLatest = () => {
+  const handleJumpToLatest = useCallback(() => {
     if (eventId) {
       navigateRoom(room.roomId, undefined, { replace: true });
     }
     setTimeline(getInitialTimeline(room));
     scrollToBottomRef.current.count += 1;
     scrollToBottomRef.current.smooth = false;
-  };
+  }, [eventId, navigateRoom, room]);
 
-  const handleJumpToUnread = () => {
+  const handleJumpToUnread = useCallback(() => {
     if (unreadInfo?.readUptoEventId) {
       setTimeline(getEmptyTimeline());
       loadEventTimeline(unreadInfo.readUptoEventId);
     }
-  };
+  }, [unreadInfo, loadEventTimeline]);
 
-  const handleMarkAsRead = () => {
+  const handleMarkAsRead = useCallback(() => {
     markAsRead(mx, room.roomId, hideActivity);
-  };
+  }, [mx, room, hideActivity]);
 
   const handleOpenReply: MouseEventHandler = useCallback(
     async (evt) => {

src/app/features/room/msgContent.ts

@@ -50,7 +50,7 @@ export const getImageMsgContent = async (
 ): Promise<IContent> => {
   const { file, originalFile, encInfo, metadata } = item;
   const [imgError, imgEl] = await to(loadImageElement(getImageFileUrl(originalFile)));
-  if (imgError) console.warn('Failed to load image element:', imgError.message);
+  if (imgError) console.warn('Failed to load image element:', imgError.name, imgError.message);
 
   const content: IContent = {
     msgtype: MsgType.Image,
@@ -85,7 +85,8 @@ export const getVideoMsgContent = async (
   const { file, originalFile, encInfo, metadata } = item;
 
   const [videoError, videoEl] = await to(loadVideoElement(getVideoFileUrl(originalFile)));
-  if (videoError) console.warn('Failed to load video element:', videoError.message);
+  if (videoError)
+    console.warn('Failed to load video element:', videoError.name, videoError.message);
 
   const content: IContent = {
     msgtype: MsgType.Video,
@@ -109,7 +110,8 @@ export const getVideoMsgContent = async (
         scaleYDimension(videoEl.videoWidth, 512, videoEl.videoHeight),
       );
     }
-    if (thumbError) console.warn('Failed to generate video thumbnail:', thumbError.message);
+    if (thumbError)
+      console.warn('Failed to generate video thumbnail:', thumbError.name, thumbError.message);
     content.info = {
       ...getVideoInfo(videoEl, file),
       ...thumbContent,

src/app/hooks/useCallEmbed.ts

@@ -3,6 +3,7 @@ import { MatrixClient, Room } from 'matrix-js-sdk';
 import { useSetAtom } from 'jotai';
 import {
   CallEmbed,
+  CallLoadErrorReason,
   ElementCallThemeKind,
   ElementWidgetActions,
   useClientWidgetApiEvent,
@@ -156,6 +157,26 @@ export const useCallJoined = (embed?: CallEmbed): boolean => {
   return joined;
 };
 
+/**
+ * Surfaces a load failure (watchdog timeout or iframe error) from the embedded
+ * Element Call iframe so the UI can show a recovery affordance instead of an
+ * indefinite "Loading..." spinner.
+ */
+export const useCallLoadError = (embed?: CallEmbed): CallLoadErrorReason | undefined => {
+  const [error, setError] = useState<CallLoadErrorReason | undefined>(() => embed?.loadFailed);
+
+  useEffect(() => {
+    if (!embed) {
+      setError(undefined);
+      return undefined;
+    }
+    setError(embed.loadFailed);
+    return embed.onLoadError((reason) => setError(reason));
+  }, [embed]);
+
+  return error;
+};
+
 export const useCallHangupEvent = (embed: CallEmbed, callback: () => void) => {
   useClientWidgetApiEvent(embed.call, ElementWidgetActions.HangupCall, callback);
   useClientWidgetApiEvent(embed.call, ElementWidgetActions.Close, callback);

src/app/hooks/usePresenceUpdater.ts

@@ -23,6 +23,13 @@ export function usePresenceUpdater() {
     const readStatus = () =>
       userId ? (localStorage.getItem(`lotus-status-msg-${userId}`) ?? '') : '';
 
+    // Log presence failures without leaking PII (user id, token, status message).
+    const warnPresenceFailure = (presence: string, err: unknown) => {
+      const reason =
+        err instanceof Error ? err.message : typeof err === 'string' ? err : 'unknown error';
+      console.warn(`Failed to set presence to "${presence}":`, reason);
+    };
+
     const setOnline = () => {
       const status = readStatus();
       return mx
@@ -30,7 +37,7 @@ export function usePresenceUpdater() {
           presence: 'online',
           ...(status ? { status_msg: status } : {}),
         })
-        .catch(() => undefined);
+        .catch((err) => warnPresenceFailure('online', err));
     };
     const setUnavailable = (statusMsg?: string) => {
       const status = readStatus();
@@ -39,10 +46,12 @@ export function usePresenceUpdater() {
           presence: 'unavailable',
           ...(statusMsg ? { status_msg: statusMsg } : status ? { status_msg: status } : {}),
         })
-        .catch(() => undefined);
+        .catch((err) => warnPresenceFailure('unavailable', err));
     };
     const setOffline = () =>
-      mx.setPresence({ presence: 'offline', status_msg: '' }).catch(() => undefined);
+      mx
+        .setPresence({ presence: 'offline', status_msg: '' })
+        .catch((err) => warnPresenceFailure('offline', err));
 
     // Manual presence overrides — no activity tracking needed.
     if (hidePresence || presenceStatus === 'invisible') {
@@ -100,6 +109,11 @@ export function usePresenceUpdater() {
       const baseUrl = mx.getHomeserverUrl();
       if (!userId || !token || !baseUrl) return;
 
+      // Reliable delivery during page teardown: navigator.sendBeacon cannot set the
+      // Authorization header required by the authenticated Matrix presence endpoint, so
+      // it isn't usable here. fetch(..., { keepalive: true }) lets the request outlive the
+      // page and is the correct mechanism for an authed endpoint. (keepalive bodies are
+      // capped at 64KB, which this tiny payload is well under.)
       fetch(`${baseUrl}/_matrix/client/v3/presence/${encodeURIComponent(userId)}/status`, {
         method: 'PUT',
         headers: {
@@ -108,7 +122,7 @@ export function usePresenceUpdater() {
         },
         body: JSON.stringify({ presence: 'offline' }),
         keepalive: true,
-      }).catch(() => undefined);
+      }).catch((err) => warnPresenceFailure('offline (pagehide)', err));
     };
 
     setOnline();

src/app/plugins/call/CallEmbed.ts

@@ -28,6 +28,14 @@ import {
 import { CallControl } from './CallControl';
 import { CallControlState } from './CallControlState';
 
+// Maximum time to wait for the embedded Element Call iframe to progress from
+// initial load to a ready/joined state. If it hasn't by then, we assume the
+// iframe has hung (e.g. blocked network, crashed widget, blank "Loading...")
+// and surface a recoverable error instead of an indefinite spinner.
+const CALL_LOAD_WATCHDOG_MS = 25_000;
+
+export type CallLoadErrorReason = 'timeout' | 'iframe';
+
 export class CallEmbed {
   private mx: MatrixClient;
 
@@ -55,6 +63,15 @@ export class CallEmbed {
 
   private themeKind: ElementCallThemeKind = 'dark';
 
+  // Watchdog: detects an iframe that never reaches a usable state.
+  private loadWatchdog?: ReturnType<typeof setTimeout>;
+
+  private loadSettled = false;
+
+  private loadError?: CallLoadErrorReason;
+
+  private readonly loadErrorListeners = new Set<(reason: CallLoadErrorReason) => void>();
+
   // Arrow-function class fields so dispose() passes the exact same reference to mx.off()
   private readonly boundOnEvent = (ev: MatrixEvent) => this.onEvent(ev);
 
@@ -218,6 +235,19 @@ export class CallEmbed {
     iframe.onload = () => {
       this.control.startObserving();
     };
+    // If the iframe document itself fails to load, fail fast.
+    iframe.onerror = () => {
+      this.settleLoad('iframe');
+    };
+
+    // Clear the watchdog as soon as the call reaches any usable state. The
+    // happy path (onCallJoined) clears it too; these cover earlier signals so a
+    // user sitting in the lobby/prescreen isn't flagged as an error.
+    this.disposables.push(this.onReady(() => this.settleLoad()));
+    this.disposables.push(this.onCapabilitiesNotified(() => this.settleLoad()));
+    this.disposables.push(this.onPreparingError(() => this.settleLoad('iframe')));
+
+    this.startLoadWatchdog();
 
     let initialMediaEvent = true;
     this.disposables.push(
@@ -314,6 +344,8 @@ export class CallEmbed {
     this.disposables.forEach((disposable) => {
       disposable();
     });
+    this.clearLoadWatchdog();
+    this.loadErrorListeners.clear();
     this.styleRetryObserver?.disconnect();
     this.call.stop();
     this.container.removeChild(this.iframe);
@@ -329,7 +361,57 @@ export class CallEmbed {
     this.eventsToFeed = new WeakSet<MatrixEvent>();
   }
 
+  private startLoadWatchdog(): void {
+    if (this.loadWatchdog !== undefined) return;
+    this.loadWatchdog = setTimeout(() => {
+      this.settleLoad('timeout');
+    }, CALL_LOAD_WATCHDOG_MS);
+  }
+
+  private clearLoadWatchdog(): void {
+    if (this.loadWatchdog !== undefined) {
+      clearTimeout(this.loadWatchdog);
+      this.loadWatchdog = undefined;
+    }
+  }
+
+  /**
+   * Marks the load lifecycle as settled. Called on success (no reason) or on
+   * failure (reason set). Idempotent so the first signal wins.
+   */
+  private settleLoad(reason?: CallLoadErrorReason): void {
+    if (this.loadSettled) return;
+    this.loadSettled = true;
+    this.clearLoadWatchdog();
+    if (reason) {
+      this.loadError = reason;
+      this.loadErrorListeners.forEach((cb) => cb(reason));
+    }
+  }
+
+  /**
+   * Whether the call failed to load within the watchdog window or errored.
+   */
+  public get loadFailed(): CallLoadErrorReason | undefined {
+    return this.loadError;
+  }
+
+  /**
+   * Subscribe to load-failure events (watchdog timeout or iframe error). If the
+   * load has already failed by the time of subscription, the callback fires
+   * immediately so late subscribers still see the error.
+   * @returns an unsubscribe function.
+   */
+  public onLoadError(callback: (reason: CallLoadErrorReason) => void): () => void {
+    this.loadErrorListeners.add(callback);
+    if (this.loadError) callback(this.loadError);
+    return () => {
+      this.loadErrorListeners.delete(callback);
+    };
+  }
+
   private onCallJoined(): void {
+    this.settleLoad();
     this.joined = true;
     this.applyStyles();
     this.control.startObserving();

src/app/utils/matrix.ts

@@ -5,6 +5,7 @@ import {
 } from 'browser-encrypt-attachment';
 import {
   EventTimeline,
+  EventType,
   MatrixClient,
   MatrixError,
   MatrixEvent,
@@ -15,7 +16,7 @@ import {
 } from 'matrix-js-sdk';
 import to from 'await-to-js';
 import { IImageInfo, IThumbnailContent, IVideoInfo } from '../../types/matrix/common';
-import { AccountDataEvent } from '../../types/matrix/accountData';
+import { MDirectContent } from '../../types/matrix/accountData';
 import { getStateEvent } from './room';
 import { Membership, StateEvent } from '../../types/matrix/room';
 
@@ -145,6 +146,42 @@ export type ContentUploadOptions = {
   onError: (error: MatrixError) => void;
 };
 
+// Build a MatrixError defensively from an unexpected upload response.
+// MatrixError's constructor expects an IErrorJson ({ errcode?, error?, ... }), not a
+// raw UploadResponse, so we guard the shape and only forward string fields it understands.
+const matrixErrorFromUploadResponse = (data: UploadResponse): MatrixError => {
+  const errorJson: { errcode?: string; error?: string } = {};
+  const maybe = data as Partial<{ errcode: unknown; error: unknown }>;
+  if (typeof maybe.errcode === 'string') errorJson.errcode = maybe.errcode;
+  if (typeof maybe.error === 'string') errorJson.error = maybe.error;
+  if (!errorJson.error) errorJson.error = 'Upload failed: missing content_uri in response';
+  return new MatrixError(errorJson);
+};
+
+const matrixErrorFromUnknown = (e: unknown): MatrixError => {
+  if (e instanceof MatrixError) return e;
+  const err = e as Partial<{ message: unknown; errcode: unknown }> | null | undefined;
+  const error = typeof err?.message === 'string' ? err.message : 'Upload failed';
+  const errcode = typeof err?.errcode === 'string' ? err.errcode : undefined;
+  return new MatrixError({ error, errcode });
+};
+
+// HTTP statuses that should not be retried — client errors are deterministic
+// (e.g. 413 payload too large, 400 bad request, 401/403 auth) and won't succeed on retry.
+const isRetryableUploadError = (e: unknown): boolean => {
+  if (e instanceof MatrixError) {
+    const status = e.httpStatus;
+    // No status => network/transport failure (transient): retry.
+    if (typeof status !== 'number') return true;
+    // Retry on rate-limiting and server-side (5xx) errors only.
+    return status === 429 || status >= 500;
+  }
+  // Non-Matrix errors are typically network/transport failures: retry.
+  return true;
+};
+
+const UPLOAD_MAX_RETRY_COUNT = 3;
+
 export const uploadContent = async (
   mx: MatrixClient,
   file: TUploadContent,
@@ -152,6 +189,14 @@ export const uploadContent = async (
 ) => {
   const { name, fileType, hideFilename, onProgress, onPromise, onSuccess, onError } = options;
 
+  const sleepForMs = (ms: number) =>
+    new Promise((resolve) => {
+      setTimeout(resolve, ms);
+    });
+
+  let lastError: MatrixError | undefined;
+
+  for (let retryCount = 0; retryCount <= UPLOAD_MAX_RETRY_COUNT; retryCount += 1) {
     const uploadPromise = mx.uploadContent(file, {
       name,
       type: fileType,
@@ -159,16 +204,38 @@ export const uploadContent = async (
       progressHandler: onProgress,
     });
     onPromise?.(uploadPromise);
+
     try {
+      // eslint-disable-next-line no-await-in-loop
       const data = await uploadPromise;
       const mxc = data.content_uri;
-    if (mxc) onSuccess(mxc);
+      if (mxc) {
-    else onError(new MatrixError(data));
+        onSuccess(mxc);
-  } catch (e: any) {
+        return;
-    const error = typeof e?.message === 'string' ? e.message : undefined;
-    const errcode = typeof e?.name === 'string' ? e.message : undefined;
-    onError(new MatrixError({ error, errcode }));
       }
+      // Missing content_uri is not a transient failure — fail immediately.
+      onError(matrixErrorFromUploadResponse(data));
+      return;
+    } catch (e: unknown) {
+      lastError = matrixErrorFromUnknown(e);
+
+      if (retryCount === UPLOAD_MAX_RETRY_COUNT || !isRetryableUploadError(e)) {
+        onError(lastError);
+        return;
+      }
+
+      // Respect server Retry-After header; fall back to capped exponential backoff,
+      // mirroring rateLimitedActions (min(1000 * 2^retryCount, 30_000)ms).
+      const waitMS =
+        (e instanceof MatrixError ? e.getRetryAfterMs() : null) ??
+        Math.min(1000 * 2 ** retryCount, 30_000);
+      // eslint-disable-next-line no-await-in-loop
+      await sleepForMs(waitMS);
+    }
+  }
+
+  // Unreachable in practice, but keeps onError guaranteed if the loop exits.
+  if (lastError) onError(lastError);
 };
 
 export const matrixEventByRecency = (m1: MatrixEvent, m2: MatrixEvent) => m2.getTs() - m1.getTs();
@@ -230,11 +297,11 @@ export const addRoomIdToMDirect = async (
   roomId: string,
   userId: string,
 ): Promise<void> => {
-  const mDirectsEvent = mx.getAccountData(AccountDataEvent.Direct as any);
+  const mDirectsEvent = mx.getAccountData(EventType.Direct);
-  let userIdToRoomIds: Record<string, string[]> = {};
+  let userIdToRoomIds: MDirectContent = {};
 
   if (typeof mDirectsEvent !== 'undefined')
-    userIdToRoomIds = structuredClone(mDirectsEvent.getContent());
+    userIdToRoomIds = structuredClone(mDirectsEvent.getContent<MDirectContent>());
 
   // remove it from the lists of any others users
   // (it can only be a DM room for one person)
@@ -255,15 +322,15 @@ export const addRoomIdToMDirect = async (
   }
   userIdToRoomIds[userId] = roomIds;
 
-  await mx.setAccountData(AccountDataEvent.Direct as any, userIdToRoomIds as any);
+  await mx.setAccountData(EventType.Direct, userIdToRoomIds);
 };
 
 export const removeRoomIdFromMDirect = async (mx: MatrixClient, roomId: string): Promise<void> => {
-  const mDirectsEvent = mx.getAccountData(AccountDataEvent.Direct as any);
+  const mDirectsEvent = mx.getAccountData(EventType.Direct);
-  let userIdToRoomIds: Record<string, string[]> = {};
+  let userIdToRoomIds: MDirectContent = {};
 
   if (typeof mDirectsEvent !== 'undefined')
-    userIdToRoomIds = structuredClone(mDirectsEvent.getContent());
+    userIdToRoomIds = structuredClone(mDirectsEvent.getContent<MDirectContent>());
 
   Object.keys(userIdToRoomIds).forEach((targetUserId) => {
     const roomIds = userIdToRoomIds[targetUserId];
@@ -273,7 +340,7 @@ export const removeRoomIdFromMDirect = async (mx: MatrixClient, roomId: string):
     }
   });
 
-  await mx.setAccountData(AccountDataEvent.Direct as any, userIdToRoomIds as any);
+  await mx.setAccountData(EventType.Direct, userIdToRoomIds);
 };
 
 export const mxcUrlToHttp = (