fix(senderkey): backfill missing key bundles on mount + refresh on incoming bundle

apps/desktop/src-tauri/tauri.conf.json

@@ -1,7 +1,7 @@
 {
   "$schema": "https://schema.tauri.app/config/2",
   "productName": "ChatApp",
-  "version": "0.3.7",
+  "version": "0.3.8",
   "identifier": "com.meinname.chatapp",
   "build": {
     "beforeDevCommand": "pnpm vite:dev",

apps/desktop/src/lib/conversationKeySync.ts

@@ -5,16 +5,24 @@ import { pgHexToBytes } from '@chat-app/shared/supabase';
 import { devLocalSecretStore } from './secretStore';
 import { supabase } from './supabase';
 
-// Watches the `devices` table for INSERTs and, whenever a peer registers a
+// Watches the `devices` table for new entries AND, on mount, scans every
-// new device that's in any of our conversations, wraps the active
+// conversation we participate in for missing key bundles. Fills gaps by
-// conversation key for the freshly-arrived device. This makes Sender-Key
+// re-wrapping our active conv-key for the missing recipient devices.
-// onboarding "just work" — the new device picks up the bundle from
-// `conversation_keys` and can decrypt the entire history once at least one
-// of our existing devices was online to do the wrapping.
 //
-// At-least-once delivery: if no existing device of any participant is online
+// This fixes the "cannot decrypt" cliff for devices that registered while
-// at the moment the new device joins, the new device stays unable to decrypt
+// no other participant device was online to share the key with them.
-// until SOMEONE comes online and runs this loop. Standard Signal trade-off.
+
+interface SyncCtx {
+  myUserId: string;
+  myDeviceId: string;
+  priv: Uint8Array;
+}
+
+// db-types is stale for `conversation_keys`/`active_key_version`; bypass.
+function rawFrom(table: string) {
+  // eslint-disable-next-line @typescript-eslint/no-explicit-any
+  return (supabase as unknown as { from: (t: string) => any }).from(table);
+}
 
 export function startConversationKeySync(
   ownUserId: string,
@@ -23,8 +31,13 @@ export function startConversationKeySync(
   let cancelled = false;
   let priv: Uint8Array | null = null;
 
-  void loadDevicePrivateKey(devLocalSecretStore, ownUserId, ownDeviceId).then((pk) => {
+  void loadDevicePrivateKey(devLocalSecretStore, ownUserId, ownDeviceId).then(async (pk) => {
+    if (cancelled) return;
     priv = pk;
+    if (!priv) return;
+    // Run a full backfill once we have the private key — covers devices that
+    // registered while we were offline.
+    await syncAllExistingGaps({ myUserId: ownUserId, myDeviceId: ownDeviceId, priv });
   });
 
   const channel = supabase
@@ -36,73 +49,164 @@ export function startConversationKeySync(
         if (cancelled) return;
         const row = payload.new;
         if (!row?.id || !row.user_id || !row.public_key) return;
-        // Skip our own devices — we don't need to send keys to ourselves
-        // (each install bootstraps its own keys via getOrCreateConvKey).
         if (row.user_id === ownUserId && row.id === ownDeviceId) return;
-        void wrapKeysForNewDevice(ownUserId, ownDeviceId, row.id, row.user_id, row.public_key);
+        if (!priv) return; // backfill on mount will catch it later
+        void wrapForOneDevice(
+          { myUserId: ownUserId, myDeviceId: ownDeviceId, priv },
+          row.id,
+          row.user_id,
+          row.public_key,
+        );
       },
     )
     .subscribe();
 
-  async function wrapKeysForNewDevice(
-    myUserId: string,
-    myDeviceId: string,
-    newDeviceId: string,
-    newDeviceUserId: string,
-    newDevicePubKeyHex: string,
-  ) {
-    if (!priv) {
-      priv = await loadDevicePrivateKey(devLocalSecretStore, myUserId, myDeviceId);
-      if (!priv) return;
-    }
-    const newPub = pgHexToBytes(newDevicePubKeyHex);
-    const ownCtx: OwnDeviceCtx = {
-      userId: myUserId,
-      deviceId: myDeviceId,
-      privateKey: priv,
-    };
-
-    // Find conversations I'm in that the new device's user is also in.
-    const { data: shared, error: sErr } = await supabase
-      .from('conversation_members')
-      .select('conversation_id')
-      .eq('user_id', newDeviceUserId);
-    if (sErr) {
-      console.warn('keySync member lookup failed', sErr);
-      return;
-    }
-    const peerConvs = new Set((shared ?? []).map((r) => r.conversation_id as string));
-    if (peerConvs.size === 0) return;
-
-    const { data: mine, error: mErr } = await supabase
-      .from('conversation_members')
-      .select('conversation_id')
-      .eq('user_id', myUserId)
-      .eq('accepted', true);
-    if (mErr) {
-      console.warn('keySync own-member lookup failed', mErr);
-      return;
-    }
-
-    const targets: string[] = [];
-    for (const row of mine ?? []) {
-      const id = row.conversation_id as string;
-      if (peerConvs.has(id)) targets.push(id);
-    }
-
-    for (const convId of targets) {
-      try {
-        await shareConvKeyToDevice(supabase, convId, newDeviceId, newPub, ownCtx);
-      } catch (err: unknown) {
-        // Common: this device has no key for that conv yet (was offline at
-        // bootstrap). Other online devices will handle it.
-        console.warn('shareConvKeyToDevice failed', { convId, err });
-      }
-    }
-  }
-
   return () => {
     cancelled = true;
     void supabase.removeChannel(channel);
   };
 }
+
+async function listMyConversationIds(myUserId: string): Promise<string[]> {
+  const { data, error } = await supabase
+    .from('conversation_members')
+    .select('conversation_id')
+    .eq('user_id', myUserId)
+    .eq('accepted', true);
+  if (error) {
+    console.warn('keySync: own-member lookup failed', error);
+    return [];
+  }
+  return (data ?? []).map((r) => r.conversation_id as string);
+}
+
+async function listConversationDevices(
+  conversationId: string,
+): Promise<{ id: string; user_id: string; public_key: string }[]> {
+  const { data: members, error: mErr } = await supabase
+    .from('conversation_members')
+    .select('user_id')
+    .eq('conversation_id', conversationId)
+    .eq('accepted', true);
+  if (mErr) {
+    console.warn('keySync: members lookup failed', mErr);
+    return [];
+  }
+  const userIds = (members ?? []).map((m) => m.user_id as string);
+  if (userIds.length === 0) return [];
+
+  const { data: devices, error: dErr } = await supabase
+    .from('devices')
+    .select('id, user_id, public_key')
+    .in('user_id', userIds);
+  if (dErr) {
+    console.warn('keySync: devices lookup failed', dErr);
+    return [];
+  }
+  return (devices ?? []) as { id: string; user_id: string; public_key: string }[];
+}
+
+async function listExistingKeyRecipients(
+  conversationId: string,
+  keyVersion: number,
+): Promise<Set<string>> {
+  const { data, error } = await rawFrom('conversation_keys')
+    .select('recipient_device_id')
+    .eq('conversation_id', conversationId)
+    .eq('key_version', keyVersion);
+  if (error) {
+    console.warn('keySync: existing keys lookup failed', error);
+    return new Set();
+  }
+  return new Set((data ?? []).map((r: { recipient_device_id: string }) => r.recipient_device_id));
+}
+
+async function getActiveKeyVersion(conversationId: string): Promise<number> {
+  const { data, error } = await rawFrom('conversations')
+    .select('active_key_version')
+    .eq('id', conversationId)
+    .single();
+  if (error) {
+    console.warn('keySync: active key version lookup failed', error);
+    return 1;
+  }
+  return (data as { active_key_version: number }).active_key_version;
+}
+
+async function syncAllExistingGaps(ctx: SyncCtx): Promise<void> {
+  const convs = await listMyConversationIds(ctx.myUserId);
+  for (const convId of convs) {
+    try {
+      await syncOneConversationGaps(ctx, convId);
+    } catch (err: unknown) {
+      console.warn('keySync: conv gap sync failed', { convId, err });
+    }
+  }
+}
+
+async function syncOneConversationGaps(ctx: SyncCtx, convId: string): Promise<void> {
+  const version = await getActiveKeyVersion(convId);
+  const devices = await listConversationDevices(convId);
+  if (devices.length === 0) return;
+
+  const recipients = await listExistingKeyRecipients(convId, version);
+  const ownCtx: OwnDeviceCtx = {
+    userId: ctx.myUserId,
+    deviceId: ctx.myDeviceId,
+    privateKey: ctx.priv,
+  };
+
+  for (const dev of devices) {
+    if (recipients.has(dev.id)) continue;
+    // Skip our own device — we already have the bundle if we're capable of
+    // sharing (or don't need it if we ourselves haven't been wrapped yet).
+    if (dev.id === ctx.myDeviceId) continue;
+    try {
+      await shareConvKeyToDevice(supabase, convId, dev.id, pgHexToBytes(dev.public_key), ownCtx);
+    } catch (err: unknown) {
+      // Most common: this device hasn't been wrapped for us yet either, so
+      // tryGetConvKey couldn't unwrap. Another peer with the key will fill
+      // the gap when they hit syncAllExistingGaps.
+      console.warn('keySync: shareConvKeyToDevice gap-fill failed', {
+        convId,
+        recipient: dev.id,
+        err,
+      });
+    }
+  }
+}
+
+async function wrapForOneDevice(
+  ctx: SyncCtx,
+  newDeviceId: string,
+  newDeviceUserId: string,
+  newDevicePubHex: string,
+): Promise<void> {
+  const myConvs = new Set(await listMyConversationIds(ctx.myUserId));
+  const { data: peerMember, error: pErr } = await supabase
+    .from('conversation_members')
+    .select('conversation_id')
+    .eq('user_id', newDeviceUserId);
+  if (pErr) {
+    console.warn('keySync: peer-member lookup failed', pErr);
+    return;
+  }
+  const sharedConvs = (peerMember ?? [])
+    .map((r) => r.conversation_id as string)
+    .filter((id) => myConvs.has(id));
+  if (sharedConvs.length === 0) return;
+
+  const newPub = pgHexToBytes(newDevicePubHex);
+  const ownCtx: OwnDeviceCtx = {
+    userId: ctx.myUserId,
+    deviceId: ctx.myDeviceId,
+    privateKey: ctx.priv,
+  };
+  for (const convId of sharedConvs) {
+    try {
+      await shareConvKeyToDevice(supabase, convId, newDeviceId, newPub, ownCtx);
+    } catch (err: unknown) {
+      console.warn('keySync: shareConvKeyToDevice failed', { convId, err });
+    }
+  }
+}

apps/desktop/src/lib/useConversationMessages.ts

@@ -238,6 +238,22 @@ export function useConversationMessages({ conversationId, userId, deviceId }: Ar
           }
         },
       )
+      // 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();
 
     return () => {