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ChatApp/apps/desktop/src/lib/useConversationMessages.ts
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import { fetchPeerPublicKeys } from '@chat-app/shared/auth';
import {
type AttachmentHandle,
type DecryptedMessage,
decryptMessages,
encryptAndUploadAttachment,
fetchConversationMessages,
insertAttachmentRow,
MAX_ATTACHMENT_BYTES,
type MessageWithCipher,
sendEncryptedMessage,
shareConvKeyToUser,
tryGetConvKey,
} from '@chat-app/shared/chat';
import { bytesToPgHex, pgBytesToBytes } from '@chat-app/shared/supabase';
import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
import { decryptBatch as decryptBatchWorker } from './decryptWorker';
import { generateWebPThumb } from './imageCompress';
import {
loadCachedMessages,
persistMessages,
pruneCache,
deleteCachedMessage,
} from './messageCache';
import {
enqueueOutbox,
getOutbox,
isDue,
markAttempt,
type OutboxItem,
removeOutbox,
shouldGiveUp,
subscribeOutbox,
} from './messageOutbox';
import { supabase } from './supabase';
import { cachedUserKey } from './userIdentity';
interface State {
messages: DecryptedMessage[];
loading: boolean;
error: string | null;
}
interface Args {
conversationId: string | undefined;
userId: string | undefined;
deviceId: string | undefined;
}
type MessageChangePayload = {
eventType: 'INSERT' | 'UPDATE' | 'DELETE';
new: Record<string, unknown>;
old: Record<string, unknown>;
};
function rowToMessage(row: Record<string, unknown>): MessageWithCipher {
return {
id: String(row.id),
conversationId: String(row.conversation_id),
senderId: String(row.sender_id),
senderDeviceId: row.sender_device_id ? String(row.sender_device_id) : null,
replyToId: row.reply_to_id ? String(row.reply_to_id) : null,
editedAt: row.edited_at ? String(row.edited_at) : null,
deletedAt: row.deleted_at ? String(row.deleted_at) : null,
createdAt: String(row.created_at),
ciphertext: pgBytesToBytes(String(row.ciphertext ?? '\\x')),
nonce: pgBytesToBytes(String(row.nonce ?? '\\x')),
keyVersion: typeof row.key_version === 'number' ? row.key_version : 1,
};
}
export function useConversationMessages({ conversationId, userId, deviceId }: Args): State & {
send: (
text: string,
images?: File[],
replyToId?: string | null,
opts?: { viewOnce?: boolean },
) => Promise<void>;
refresh: () => Promise<void>;
pending: OutboxItem[];
retryPending: (id: string) => void;
cancelPending: (id: string) => void;
} {
const [state, setState] = useState<State>({ messages: [], loading: true, error: null });
const [pending, setPending] = useState<OutboxItem[]>(() =>
conversationId ? getOutbox(conversationId) : [],
);
const privateKeyRef = useRef<Uint8Array | null>(null);
useEffect(() => {
if (!conversationId) {
setPending([]);
return;
}
return subscribeOutbox((byConv) => {
setPending(byConv[conversationId] ?? []);
});
}, [conversationId]);
// Load own user private key once per user.
useEffect(() => {
privateKeyRef.current = null;
if (!userId) return;
void cachedUserKey(userId).then((pk) => {
privateKeyRef.current = pk;
});
}, [userId]);
// Proactive rewrap sweep: when a conversation opens, walk every accepted
// member and ensure the active conv-key has a `recipient_user_id` bundle
// for them. Members who are missing one (typically peers who haven't yet
// migrated to the per-user key model) get a best-effort wrap from the
// local conv-key handle. Closes the legacy migration gap so peer B can
// read on first unlock without manual intervention from A.
useEffect(() => {
if (!conversationId || !userId) return;
let cancelled = false;
const run = async (): Promise<void> => {
// Wait for the private key ref to be populated. Loop with backoff
// because it's set asynchronously by another effect; bail if the
// conversation switches.
for (let i = 0; i < 20 && !privateKeyRef.current && !cancelled; i++) {
await new Promise((r) => setTimeout(r, 100));
}
const priv = privateKeyRef.current;
if (!priv || cancelled) return;
try {
const { data: convRow, error: convErr } = await supabase
.from('conversations')
.select('active_key_version')
.eq('id', conversationId)
.single();
if (convErr || !convRow) return;
// db-types snapshot predates the active_key_version column; cast via unknown.
const version = (convRow as unknown as { active_key_version: number }).active_key_version;
const handle = await tryGetConvKey(supabase, conversationId, userId, priv, version);
if (!handle || cancelled) return;
const { data: members, error: mErr } = await supabase
.from('conversation_members')
.select('user_id, accepted')
.eq('conversation_id', conversationId);
if (mErr || !members) return;
const memberIds = (members as Array<{ user_id: string; accepted: boolean }>)
.filter((m) => m.accepted && m.user_id !== userId)
.map((m) => m.user_id);
if (memberIds.length === 0) return;
const peers = await fetchPeerPublicKeys(supabase, memberIds);
for (const peer of peers) {
if (cancelled) return;
const { count, error: cntErr } = await (
supabase as unknown as {
from: (t: string) => {
select: (s: string, o?: object) => {
eq: (...a: unknown[]) => {
eq: (...a: unknown[]) => {
eq: (
...a: unknown[]
) => Promise<{ count: number | null; error: unknown }>;
};
};
};
};
}
)
.from('conversation_keys')
.select('recipient_user_id', { count: 'exact', head: true })
.eq('conversation_id', conversationId)
.eq('recipient_user_id', peer.userId)
.eq('key_version', version);
if (cntErr) continue;
if ((count ?? 0) === 0) {
try {
await shareConvKeyToUser(
supabase,
conversationId,
peer.userId,
peer.publicKey,
{ userId, privateKey: priv },
);
} catch (err) {
console.warn('proactive rewrap failed for', peer.userId, err);
}
}
}
} catch (err) {
console.warn('proactive rewrap sweep failed', err);
}
};
void run();
return () => {
cancelled = true;
};
}, [conversationId, userId]);
const decryptBatch = useCallback(
async (messages: MessageWithCipher[]): Promise<DecryptedMessage[]> => {
const priv = privateKeyRef.current;
if (!priv || !userId || messages.length === 0) {
return messages.map((m) => ({ ...m, plaintext: null }));
}
return decryptMessages({
client: supabase,
messages,
ownUserId: userId,
ownPrivateKey: priv,
// Offload the symmetric decrypt + utf-8 decode to a Web Worker so
// the main thread stays responsive during bulk operations (initial
// fetch, backfill after sleep).
aeadBatchDelegate: decryptBatchWorker,
});
},
[userId],
);
const refresh = useCallback(async () => {
if (!conversationId) return;
try {
// Only show the loading spinner on the *initial* fetch — subsequent
// refreshes (focus/visibility) replace messages in-place to avoid
// flickering an empty state on every wake.
setState((prev) =>
prev.messages.length === 0 ? { ...prev, loading: true } : prev,
);
const rows = await fetchConversationMessages(supabase, conversationId);
const decrypted = await decryptBatch(rows);
setState({ messages: decrypted, loading: false, error: null });
// Persist the fresh batch to the local cache so next conversation
// switch / app start can hydrate instantly. Fire-and-forget — cache
// write failure is never user-visible.
void persistMessages(conversationId, decrypted);
} catch (err: unknown) {
setState((prev) => ({
...prev,
loading: false,
error: err instanceof Error ? err.message : 'failed to load messages',
}));
}
}, [conversationId, decryptBatch]);
// Hydrate from the local SQLite cache the moment the conversation id
// changes. Runs in parallel with the network fetch — whichever resolves
// first populates the UI, and `refresh` will replace stale cache data
// when the server response lands. On cache-miss this is a ~5ms no-op.
useEffect(() => {
if (!conversationId) return;
let cancelled = false;
void loadCachedMessages(conversationId).then((cached) => {
if (cancelled || cached.length === 0) return;
setState((prev) => {
// Don't clobber a fresh server response that already landed.
if (prev.messages.length > 0) return prev;
return { messages: cached, loading: false, error: null };
});
});
return () => {
cancelled = true;
};
}, [conversationId]);
// Prune cache once per app session.
useEffect(() => {
void pruneCache();
}, []);
// Realtime INSERT handler — refetches the row via REST so we get the
// canonical bytea encoding (postgres_changes payloads serialize bytea
// differently and decoding them inline is brittle). Then decrypt + append.
// Skips if the message is already in state (e.g. optimistic insert from our
// own send), so the sender's cached copy isn't overwritten with a flicker.
const handleInsert = useCallback(
async (row: Record<string, unknown>) => {
if (!conversationId || !deviceId) return;
const id = String(row.id);
let alreadyHave = false;
setState((prev) => {
if (prev.messages.some((m) => m.id === id)) alreadyHave = true;
return prev;
});
if (alreadyHave) return;
let decrypted: DecryptedMessage | null = null;
for (let attempt = 0; attempt < 6; attempt++) {
const { data, error } = await supabase
.from('messages')
.select(
'id, conversation_id, sender_id, sender_device_id, reply_to_id, edited_at, deleted_at, created_at, ciphertext, nonce, key_version',
)
.eq('id', id)
.maybeSingle();
if (error) {
console.warn('handleInsert refetch failed', error);
return;
}
if (!data) {
await new Promise((r) => window.setTimeout(r, 120 * (attempt + 1)));
continue;
}
// db-types snapshot predates the sender-key columns; cast to bypass.
const r = data as unknown as {
id: string;
conversation_id: string;
sender_id: string;
sender_device_id: string | null;
reply_to_id: string | null;
edited_at: string | null;
deleted_at: string | null;
created_at: string;
ciphertext: string;
nonce: string;
key_version: number;
};
const msg: MessageWithCipher = {
id: r.id,
conversationId: r.conversation_id,
senderId: r.sender_id,
senderDeviceId: r.sender_device_id,
replyToId: r.reply_to_id,
editedAt: r.edited_at,
deletedAt: r.deleted_at,
createdAt: r.created_at,
ciphertext: pgBytesToBytes(String(r.ciphertext)),
nonce: pgBytesToBytes(String(r.nonce)),
keyVersion: r.key_version,
};
const [d] = await decryptBatch([msg]);
if (d) {
decrypted = d;
if (d.plaintext !== null) break;
}
await new Promise((r) => window.setTimeout(r, 200 * (attempt + 1)));
}
if (!decrypted) return;
setState((prev) => {
if (prev.messages.some((m) => m.id === decrypted!.id)) return prev;
return { ...prev, messages: [...prev.messages, decrypted!] };
});
},
[conversationId, deviceId, decryptBatch],
);
const handleUpdate = useCallback(
async (row: Record<string, unknown>) => {
const partial = rowToMessage(row);
setState((prev) => {
const idx = prev.messages.findIndex((m) => m.id === partial.id);
if (idx === -1) return prev;
const existing = prev.messages[idx];
if (!existing) return prev;
const next = [...prev.messages];
next[idx] = {
...existing,
editedAt: partial.editedAt,
deletedAt: partial.deletedAt,
};
return { ...prev, messages: next };
});
if (partial.editedAt && !partial.deletedAt) {
// Realtime bytea encoding varies (base64 vs hex, even null for
// unchanged columns on some configs). Refetch via REST to get the
// canonical `\x…` hex then decrypt — same pattern as handleInsert.
if (!conversationId || !deviceId) return;
let decrypted: DecryptedMessage | null = null;
for (let attempt = 0; attempt < 6; attempt++) {
const { data, error } = await supabase
.from('messages')
.select(
'id, conversation_id, sender_id, sender_device_id, reply_to_id, edited_at, deleted_at, created_at, ciphertext, nonce, key_version',
)
.eq('id', partial.id)
.maybeSingle();
if (error) {
console.warn('handleUpdate refetch failed', error);
return;
}
if (!data) {
await new Promise((r) => window.setTimeout(r, 120 * (attempt + 1)));
continue;
}
const r = data as unknown as {
id: string;
conversation_id: string;
sender_id: string;
sender_device_id: string | null;
reply_to_id: string | null;
edited_at: string | null;
deleted_at: string | null;
created_at: string;
ciphertext: string;
nonce: string;
key_version: number;
};
const msg: MessageWithCipher = {
id: r.id,
conversationId: r.conversation_id,
senderId: r.sender_id,
senderDeviceId: r.sender_device_id,
replyToId: r.reply_to_id,
editedAt: r.edited_at,
deletedAt: r.deleted_at,
createdAt: r.created_at,
ciphertext: pgBytesToBytes(String(r.ciphertext)),
nonce: pgBytesToBytes(String(r.nonce)),
keyVersion: r.key_version,
};
const [d] = await decryptBatch([msg]);
if (d) {
decrypted = d;
if (d.plaintext !== null) break;
}
await new Promise((r) => window.setTimeout(r, 200 * (attempt + 1)));
}
if (!decrypted) return;
setState((prev) => {
const idx = prev.messages.findIndex((m) => m.id === decrypted!.id);
if (idx === -1) return prev;
const next = [...prev.messages];
next[idx] = decrypted!;
return { ...prev, messages: next };
});
}
},
[conversationId, deviceId, decryptBatch],
);
const handleDelete = useCallback((row: Record<string, unknown>) => {
const id = String(row.id);
setState((prev) => ({
...prev,
messages: prev.messages.filter((m) => m.id !== id),
}));
void deleteCachedMessage(id);
}, []);
useEffect(() => {
if (!conversationId || !userId || !deviceId) return;
void refresh();
// Batch INSERT bursts so a paste / backfill doesn't fire N parallel
// refetches + decrypts. If more than BATCH_BURST_THRESHOLD ids arrive
// within BATCH_WINDOW_MS, collapse to a single refresh() which pulls
// the last 100 in one query — cheaper and keeps order stable. For
// lone inserts the per-id path stays so latency is unchanged.
const BATCH_WINDOW_MS = 250;
const BATCH_BURST_THRESHOLD = 3;
let burstBuffer: Array<Record<string, unknown>> = [];
let burstTimer: number | null = null;
const flushBurst = () => {
const buf = burstBuffer;
burstBuffer = [];
if (burstTimer !== null) {
window.clearTimeout(burstTimer);
burstTimer = null;
}
if (buf.length === 0) return;
if (buf.length > BATCH_BURST_THRESHOLD) {
void refresh();
} else {
for (const row of buf) void handleInsert(row);
}
};
const queueInsert = (row: Record<string, unknown>) => {
burstBuffer.push(row);
if (burstTimer === null) {
burstTimer = window.setTimeout(flushBurst, BATCH_WINDOW_MS);
}
};
const channel = supabase
.channel('conv:' + conversationId)
.on(
'postgres_changes',
{
event: '*',
schema: 'public',
table: 'messages',
filter: 'conversation_id=eq.' + conversationId,
},
(payload: MessageChangePayload) => {
if (payload.eventType === 'INSERT') {
queueInsert(payload.new);
} else if (payload.eventType === 'UPDATE') {
void handleUpdate(payload.new);
} else if (payload.eventType === 'DELETE') {
handleDelete(payload.old);
}
},
)
// When a peer device wraps the conversation-key for us (e.g. we just
// registered a fresh device), re-decrypt the visible messages.
.on(
'postgres_changes',
{
event: 'INSERT',
schema: 'public',
table: 'conversation_keys',
filter: 'conversation_id=eq.' + conversationId,
},
(payload: { new: { recipient_device_id?: string } }) => {
if (payload.new?.recipient_device_id === deviceId) {
void refresh();
}
},
)
.subscribe();
// Refresh + reconnect on wake from background throttle (mostly Windows
// WebView2). Without this, messages inserted while the window is
// minimised never arrive until the user explicitly reloads. Throttled to
// at most once per AWAKE_THROTTLE_MS so the inevitable cluster of
// visibility/online events on focus does not cause a flicker storm.
let lastAwakeRefresh = 0;
const AWAKE_THROTTLE_MS = 30_000;
const onAwake = () => {
if (document.visibilityState !== 'visible') return;
const now = Date.now();
if (now - lastAwakeRefresh < AWAKE_THROTTLE_MS) return;
lastAwakeRefresh = now;
void refresh();
try {
channel.subscribe();
} catch {
/* already live */
}
};
document.addEventListener('visibilitychange', onAwake);
window.addEventListener('online', onAwake);
return () => {
if (burstTimer !== null) window.clearTimeout(burstTimer);
document.removeEventListener('visibilitychange', onAwake);
window.removeEventListener('online', onAwake);
void supabase.removeChannel(channel);
};
}, [conversationId, userId, deviceId, refresh, handleInsert, handleUpdate, handleDelete]);
const sendText = useCallback(
async (convId: string, uid: string, did: string, priv: Uint8Array, text: string, replyToId: string | null): Promise<void> => {
const msg = await sendEncryptedMessage({
client: supabase,
conversationId: convId,
plaintext: text,
senderUserId: uid,
senderDeviceId: did,
senderPrivateKey: priv,
...(replyToId ? { replyToId } : {}),
});
setState((prev) => {
if (prev.messages.some((m) => m.id === msg.id)) return prev;
return {
...prev,
messages: [
...prev.messages,
{ ...msg, plaintext: text } as DecryptedMessage,
],
};
});
},
[],
);
const send = useCallback(
async (
text: string,
images: File[] = [],
replyToId: string | null = null,
opts: { viewOnce?: boolean } = {},
) => {
const trimmed = text.trim();
if ((!trimmed && images.length === 0) || !conversationId || !userId || !deviceId) return;
const priv = privateKeyRef.current;
if (!priv) throw new Error('private key not loaded');
// Slash-command: /tempmsg <seconds> <text> sends an ephemeral message
// that the sender auto-deletes after the window elapses. Both peers
// see the countdown via the expireMs field embedded in the plaintext
// payload — no server support required.
const tempMatch = /^\/tempmsg\s+(\d+)\s+([\s\S]+)$/i.exec(trimmed);
if (tempMatch && images.length === 0) {
const seconds = Math.min(3600, Math.max(5, parseInt(tempMatch[1]!, 10)));
const body = tempMatch[2]!.trim();
const payload = JSON.stringify({
v: 1,
type: 'text',
text: body,
attachments: [],
expireMs: seconds * 1000,
});
try {
await sendText(conversationId, userId, deviceId, priv, payload, replyToId);
} catch (err: unknown) {
const msg = err instanceof Error ? err.message : 'send failed';
enqueueOutbox({
conversationId,
text: payload,
replyToId,
error: msg,
});
}
return;
}
// Text-only path is retryable — if the network is down or the server
// rejects transiently, stash in the outbox and keep the UI optimistic.
// Attachments can't be deferred (large payloads, uploaded separately),
// so those still surface the error immediately.
if (images.length === 0) {
try {
await sendText(conversationId, userId, deviceId, priv, trimmed, replyToId);
} catch (err: unknown) {
const msg = err instanceof Error ? err.message : 'send failed';
enqueueOutbox({
conversationId,
text: trimmed,
replyToId,
error: msg,
});
}
return;
}
// 1. Upload + encrypt each image. Collect handles + raw blob nonces
// (so the public attachment row can reference the blob-level nonce).
const handles: AttachmentHandle[] = [];
const blobNonceHexByHandleId = new Map<string, string>();
for (const file of images) {
if (file.size > MAX_ATTACHMENT_BYTES) {
throw new Error('attachment exceeds max size (10 MB)');
}
const dims = await readImageDimensions(file);
// Phase 6B: generate a small WebP preview thumb so the receiver's
// bubble loads fast (typical 320×240 WebP is 1030KB vs the full
// image's 110MB). `generateWebPThumb` short-circuits to null on
// non-images, animated formats, and small files — and on failure;
// the upload helper then just skips the second upload.
const thumbBlob = await generateWebPThumb(file);
const res = await encryptAndUploadAttachment({
client: supabase,
conversationId,
file,
mimeType: file.type || 'application/octet-stream',
sizeBytes: file.size,
...(dims.width !== undefined ? { width: dims.width } : {}),
...(dims.height !== undefined ? { height: dims.height } : {}),
...(thumbBlob ? { thumbBlob } : {}),
});
// Stamp the view-once flag on each handle the caller requested it
// for. The flag rides inside the encrypted payload (so peers can
// render the locked card without leaking who-sent-what to the
// server) AND lands on the public message_attachments row via
// insertAttachmentRow below (where the mark-viewed RPC enforces it).
if (opts.viewOnce) {
res.handle.viewOnce = true;
}
handles.push(res.handle);
blobNonceHexByHandleId.set(res.handle.id, bytesToPgHex(res.nonce));
}
// 2. Send message (inserts messages + per-conversation key bundles).
const msg = await sendEncryptedMessage({
client: supabase,
conversationId,
plaintext: trimmed,
senderUserId: userId,
senderDeviceId: deviceId,
senderPrivateKey: priv,
...(handles.length > 0 ? { attachmentHandles: handles } : {}),
...(replyToId ? { replyToId } : {}),
});
// 3. Optimistic insert — we already have the plaintext in hand and the
// server returned the row id, so add the message to local state
// immediately. Realtime will then no-op (handleInsert dedupes by id).
const attachmentsPayload =
handles.length === 0
? trimmed
: JSON.stringify({ v: 1, text: trimmed, attachments: handles });
setState((prev) => {
if (prev.messages.some((m) => m.id === msg.id)) return prev;
return {
...prev,
messages: [
...prev.messages,
{
...msg,
plaintext: attachmentsPayload,
} as DecryptedMessage,
],
};
});
// 4. Insert public attachment metadata rows pointing at the new message.
for (const h of handles) {
const blobNonce = blobNonceHexByHandleId.get(h.id) ?? '\\x';
await insertAttachmentRow(supabase, msg.id, h, blobNonce);
}
},
[conversationId, userId, deviceId, sendText],
);
// Drain outbox: retry due items, remove on success, record attempt on fail.
// Runs on online event, window focus, and a 10s interval.
useEffect(() => {
if (!conversationId || !userId || !deviceId) return;
let draining = false;
const drain = async (): Promise<void> => {
if (draining) return;
const priv = privateKeyRef.current;
if (!priv) return;
if (typeof navigator !== 'undefined' && navigator.onLine === false) return;
draining = true;
try {
const items = getOutbox(conversationId).filter(isDue);
for (const item of items) {
if (shouldGiveUp(item)) continue;
try {
await sendText(
conversationId,
userId,
deviceId,
priv,
item.text,
item.replyToId,
);
removeOutbox(conversationId, item.id);
} catch (err: unknown) {
markAttempt(
conversationId,
item.id,
err instanceof Error ? err.message : 'send failed',
);
}
}
} finally {
draining = false;
}
};
const interval = window.setInterval(() => {
void drain();
}, 10_000);
const onOnline = () => void drain();
window.addEventListener('online', onOnline);
window.addEventListener('focus', onOnline);
// Kick once immediately on mount for stale queued items.
void drain();
return () => {
window.clearInterval(interval);
window.removeEventListener('online', onOnline);
window.removeEventListener('focus', onOnline);
};
}, [conversationId, userId, deviceId, sendText]);
const retryPending = useCallback(
(id: string) => {
if (!conversationId) return;
// Force due now; the drain loop will pick it up on next tick.
markAttempt(conversationId, id, null);
// Manual kick: mutate nextAttemptAt by re-enqueuing? Simpler — just
// trigger a drain-ish by queueing a microtask. The interval picks up
// due items within 10s, but for UX we also eagerly try here.
const priv = privateKeyRef.current;
if (!priv || !userId || !deviceId) return;
const item = getOutbox(conversationId).find((x) => x.id === id);
if (!item) return;
void (async () => {
try {
await sendText(conversationId, userId, deviceId, priv, item.text, item.replyToId);
removeOutbox(conversationId, id);
} catch (err: unknown) {
markAttempt(
conversationId,
id,
err instanceof Error ? err.message : 'send failed',
);
}
})();
},
[conversationId, userId, deviceId, sendText],
);
const cancelPending = useCallback(
(id: string) => {
if (!conversationId) return;
removeOutbox(conversationId, id);
},
[conversationId],
);
return useMemo(
() => ({ ...state, send, refresh, pending, retryPending, cancelPending }),
[state, send, refresh, pending, retryPending, cancelPending],
);
}
// Best-effort image dimension probe. Falls back silently on non-images.
async function readImageDimensions(file: File): Promise<{ width?: number; height?: number }> {
if (!file.type.startsWith('image/')) return {};
const url = URL.createObjectURL(file);
try {
return await new Promise<{ width?: number; height?: number }>((resolve) => {
const img = new Image();
img.onload = () => resolve({ width: img.naturalWidth, height: img.naturalHeight });
img.onerror = () => resolve({});
img.src = url;
});
} finally {
URL.revokeObjectURL(url);
}
}