Merge branch 'feat/call-relay-auto-peering'

Closes backlog #16. Implements sendCallRelay/sendTypingRelay auto-peering
and caller-facing dm_call_undeliverable failure surface.

See internal notes
and internal notes
for the full design + implementation plan.

docs/systems/federation.md

@@ -403,7 +403,7 @@ The `(source_instance, source_message_id)` pair is checked before insertion. Dup
 **`sendTypingRelay()` (`federationOutbox.ts`):**
 - Fetches channel's `federatedId` and `getDmParticipants()` for target resolution
 - Builds `FederationRelayEvent` with `typing: { homeUserId, homeInstance, username }`
-- Reuses `sendCallRelay()` for the actual POST to each remote peer origin
+- Calls `sendCallRelay(origin, [event], { peeringTimeoutMs: 0 })` for each remote peer origin — non-active peers are skipped and a background `ensurePeered` warm-up is kicked off instead
 
 **Inbound (`federation.ts`):**
 - `processDmTypingStartEvent` → look up channel by `federatedId`, resolve user via `resolveLocalUser()` (no stub creation for ephemeral events), broadcast `dm_typing` to local members
@@ -1024,7 +1024,20 @@ All events carry standard relay fields: `eventType`, `messageId`, `encryptionVer
 
 ### Direct Delivery (No Outbox)
 
-Call signaling is time-critical and bypasses the outbox entirely. `sendCallRelay()` sends a synchronous HTTP POST to the peer's `/api/federation/relay` endpoint using existing HMAC signing (`buildFederationHeaders`). If delivery fails, the call operation fails — there is no retry.
+**`sendCallRelay(targetPeerOrigin, events, opts?)`** (`federationOutbox.ts`):
+
+- Latency-sensitive: returns `CallRelayResult = { ok: true } | { ok: false; reason: CallRelayFailureReason; error: string }`.
+- Peering resolution:
+  1. If the peer row is `active` or `unreachable`, POST directly (the health check restores `unreachable` peers; re-handshaking is wasteful).
+  2. Otherwise race `ensurePeered` against `opts.peeringTimeoutMs` (default `CALL_PEERING_TIMEOUT_MS = 3_000` ms). The background handshake is **not** aborted on race loss — a warn-logged catch is attached so a late-rejecting background promise does not emit `unhandledRejection`.
+- Peer-state → reason mapping is exhaustive over the `EnsurePeeredResult` union (`active` / `rejected` / `pending` / `failed`) plus the external `timeout` branch. TypeScript `never` check in the switch default catches future additions. Note: the `livekit_unavailable` reason in `DmCallUndeliverableReason` is emitted separately from `sendFederatedCallStart`'s LiveKit pre-flight in `ws/events.ts`, not from this switch — `sendCallRelay` only produces `CallRelayFailureReason` values (`peer_rejected` / `peer_awaiting_approval` / `peer_transient_failure` / `post_failed`).
+- Non-blocking mode: `peeringTimeoutMs: 0` (used by typing) skips the POST for non-active peers, kicks off `ensurePeered` as a background warm-up, returns `peer_transient_failure` silently.
+
+**`sendTypingRelay(dmChannelId, eventType, userId)`**:
+
+- Fire-and-forget to each remote DM participant's home instance via `sendCallRelay(origin, [event], { peeringTimeoutMs: 0 })`. Typing is an ephemeral hint — lost packets are acceptable and there is no user-facing failure surface.
+
+**Call-start failure surfacing.** `sendFederatedCallStart` aggregates targeted-peer results and emits `dm_call_undeliverable` to the caller for failed targeted peers. See `docs/systems/voice.md` and `docs/systems/websocket.md` for the event contract.
 
 ### Call Flows
 
@@ -1157,4 +1170,8 @@ If the `federation_mutation_log` table exists but is empty, populates it with `c
 
 ## Known Issues
 
-No critical known issues. See `docs/federation-production-roadmap.md` for open items (FED-001 through FED-013).
+See `docs/federation-production-roadmap.md` for open items (FED-001 through FED-013).
+
+- **Accept-relay failure dead end.** If Bob on B accepts a call from Alice on A and the `dm_call_accept` S2S relay back to A fails, Alice's client does not exit the `outgoingCall` state until the 60 s ring timeout fires `dm_call_ended`. The client clears `outgoingCall` only on `dm_call_accepted | rejected | ended` (`useWebSocket.ts`), with no LiveKit participant-join fallback. Surfacing this requires a B-side event and call-state rollback; deferred.
+- **End-relay failure dead end.** Similar mechanism, lower severity because LiveKit `ParticipantDisconnected` typically unwinds the voice UI on the host side; local DM call state still lingers to the 60 s timeout. Deferred.
+- **Path-B reject-relay failure dead end.** Third-instance user (Carol on C) rings for a call hosted on A via Path B; if her `dm_call_reject` C→A relay fails, A never deducts her from the pending ringees, so her name persists in the caller's "still ringing" set until the 60 s timeout. Same class as accept-failure; deferred.

docs/systems/voice.md

@@ -56,7 +56,13 @@ DM calls work across federated instances. The caller's instance hosts the LiveKi
 
 ### Universal Relay
 
-All `dm_call_*` signaling events (`start`, `accept`, `reject`, `end`) are relayed to every active federation peer in parallel via `Promise.all`. Each `sendCallRelay` call has a 10-second timeout. This is a synchronous HTTP POST to the peer's federation endpoint — it bypasses the outbox worker entirely because call signaling is latency-sensitive and must not be queued.
+All `dm_call_*` signaling events (`start`, `accept`, `reject`, `end`) are relayed to every active federation peer in parallel. Each `sendCallRelay` call has a 10-second HTTP timeout. This bypasses the outbox worker — call signaling is latency-sensitive.
+
+**Auto-peering at send time.** If the target origin has no active peer record, `sendCallRelay` races an `ensurePeered` handshake against a 3 s deadline (`CALL_PEERING_TIMEOUT_MS`). On success the relay POSTs normally; on timeout it returns `peer_transient_failure` without aborting the background handshake, so a subsequent attempt typically succeeds. Typing (`sendTypingRelay`) passes `peeringTimeoutMs: 0` — the POST is skipped for non-active peers and a warm-up `ensurePeered` runs in the background.
+
+**Call-start failure surface.** `sendFederatedCallStart` aggregates results from its targeted-peer relays (peers whose origin matches a DM member's `homeInstance`) and emits a single `dm_call_undeliverable` event to the caller when any targeted peer fails. `terminal: true` (no successful targeted relay AND no connected local non-caller member) also destroys the local ring room so the caller's UI clears immediately; `terminal: false` leaves the call ringing for reachable recipients. The all-peers broadcast (Path-B fallback to non-member-hosting peers) logs failures only — they are not surfaced.
+
+Accept and end relay failures are NOT surfaced today; see the federation doc's "Known issues" section for the deferred accept-failure dead-end.
 
 ### Dual-Path Processing
 

docs/systems/websocket.md

@@ -170,6 +170,7 @@ reason: `'displaced'` (new tab) | `'session_closed'`
 | `dm_call_accepted` | dmChannelId?, federatedCallId? | DM members |
 | `dm_call_rejected` | dmChannelId?, federatedCallId? | DM members |
 | `dm_call_ended` | dmChannelId?, federatedCallId? | DM members |
+| `dm_call_undeliverable` | Sent to caller when a call-start relay to one or more targeted peers fails. `failures[]` enumerates each failed peer with a `reason` (`peer_rejected` / `peer_awaiting_approval` / `peer_transient_failure` / `livekit_unavailable`). `terminal: true` means the local ring was destroyed; `false` means the call continues for reachable recipients. | caller only |
 
 ### Social
 | type | fields | scope |

packages/server/src/utils/federationOutbox.ts

@@ -6,6 +6,7 @@ import crypto from 'node:crypto';
 import type { FederationRelayEvent, FederationRelayParticipant, FederationRelayAttachment, DmMessageWithUser, FederationRelayRequest } from '@backspace/shared';
 import { getOurOrigin, buildFederationHeaders, generateHmacSecret } from './federationAuth.js';
 import { extractDomain } from '../routes/federation.js';
+import { racePeering, ensurePeered } from './federationPeering.js';
 
 // ─── Settings Cache ──────────────────────────────────────────────────────────
 
@@ -469,28 +470,87 @@ export function buildRelayPayload(
   };
 }
 
+/** 3s budget for the on-demand handshake before a call relay POST. */
+export const CALL_PEERING_TIMEOUT_MS = 3_000;
+
+export type CallRelayFailureReason =
+  | 'peer_rejected'
+  | 'peer_awaiting_approval'
+  | 'peer_transient_failure'
+  | 'post_failed';
+
+export type CallRelayResult =
+  | { ok: true }
+  | { ok: false; reason: CallRelayFailureReason; error: string };
+
 /**
  * Send call signaling events directly to a remote peer (bypasses outbox).
- * Used for time-critical call events where latency matters.
- * If the HTTP POST fails, the call operation fails — no retry.
+ * Latency-sensitive: if no active peer exists, race an ensurePeered handshake
+ * against `opts.peeringTimeoutMs` (default CALL_PEERING_TIMEOUT_MS).
+ *
+ * `peeringTimeoutMs: 0` = non-blocking mode (used by sendTypingRelay):
+ *   - If the peer is currently active, POST. Otherwise skip the POST, kick off
+ *     ensurePeered() in the background as a warm-up, and return
+ *     { ok:false, reason:'peer_transient_failure' }.
  */
 export async function sendCallRelay(
   targetPeerOrigin: string,
   events: FederationRelayEvent[],
-): Promise<{ ok: boolean; error?: string }> {
+  opts: { peeringTimeoutMs?: number } = {},
+): Promise<CallRelayResult> {
+  const timeoutMs = opts.peeringTimeoutMs ?? CALL_PEERING_TIMEOUT_MS;
   const db = getDb();
-  const peer = db.select()
+
+  // ─── Fast path: peer already active or unreachable (health check handles) ──
+  const existing = db.select()
     .from(schema.federationPeers)
-    .where(and(
-      eq(schema.federationPeers.origin, targetPeerOrigin),
-      eq(schema.federationPeers.status, 'active'),
-    ))
+    .where(eq(schema.federationPeers.origin, targetPeerOrigin))
     .get();
 
+  let peer = existing && (existing.status === 'active' || existing.status === 'unreachable')
+    ? existing
+    : null;
+
   if (!peer) {
-    return { ok: false, error: `No active peer for origin ${targetPeerOrigin}` };
+    // ─── Non-blocking mode (typing): warm up in background, do not POST ──
+    if (timeoutMs === 0) {
+      ensurePeered(targetPeerOrigin).catch(err => {
+        console.warn('[federation] typing-triggered background handshake:', targetPeerOrigin, err);
+      });
+      return { ok: false, reason: 'peer_transient_failure', error: 'peer not active' };
+    }
+
+    // ─── Race ensurePeered against the deadline ──
+    const raced = await racePeering(targetPeerOrigin, timeoutMs);
+
+    switch (raced.status) {
+      case 'active':
+        // Re-fetch the now-active peer row for HMAC secret.
+        peer = db.select()
+          .from(schema.federationPeers)
+          .where(eq(schema.federationPeers.origin, targetPeerOrigin))
+          .get() ?? null;
+        if (!peer) {
+          return { ok: false, reason: 'peer_transient_failure', error: 'peer row missing after handshake' };
+        }
+        break;
+      case 'rejected':
+        return { ok: false, reason: 'peer_rejected', error: raced.error };
+      case 'pending':
+        return { ok: false, reason: 'peer_awaiting_approval', error: raced.error };
+      case 'failed':
+        return { ok: false, reason: 'peer_transient_failure', error: raced.error };
+      case 'timeout':
+        return { ok: false, reason: 'peer_transient_failure', error: `Peering handshake did not complete within ${(timeoutMs / 1000).toFixed(1)}s` };
+      default: {
+        // Exhaustiveness check — catches any future additions to EnsurePeeredResult.
+        const _exhaustive: never = raced;
+        return { ok: false, reason: 'peer_transient_failure', error: `unexpected peering result: ${JSON.stringify(_exhaustive)}` };
+      }
+    }
   }
 
+  // ─── POST ──────────────────────────────────────────────────────────────────
   const ourOrigin = getOurOrigin();
   const body: FederationRelayRequest = {
     version: 1,
@@ -499,7 +559,6 @@ export async function sendCallRelay(
   };
   const bodyStr = JSON.stringify(body);
 
-  // Use pending secret during rotation (FED-011), otherwise current
   const signingSecret = peer.pendingHmacSecret ?? peer.hmacSecret;
   const headers = buildFederationHeaders(bodyStr, signingSecret, ourOrigin);
 
@@ -511,14 +570,27 @@ export async function sendCallRelay(
       signal: AbortSignal.timeout(10_000),
     });
 
-    if (!res.ok) {
-      const text = await res.text().catch(() => '');
-      return { ok: false, error: `HTTP ${res.status}: ${text}` };
-    }
+    if (res.ok) return { ok: true };
 
-    return { ok: true };
+    const text = await res.text().catch(() => '');
+    if (res.status >= 400 && res.status < 500) {
+      return {
+        ok: false,
+        reason: 'post_failed',
+        error: `HTTP ${res.status}: ${text}`,
+      };
+    }
+    return {
+      ok: false,
+      reason: 'peer_transient_failure',
+      error: `HTTP ${res.status}: ${text}`,
+    };
   } catch (err) {
-    return { ok: false, error: err instanceof Error ? err.message : 'fetch_failed' };
+    return {
+      ok: false,
+      reason: 'peer_transient_failure',
+      error: err instanceof Error ? err.message : 'fetch_failed',
+    };
   }
 }
 
@@ -700,10 +772,16 @@ export async function sendTypingRelay(
     },
   };
 
-  // Fire-and-forget to each remote peer
+  // Fire-and-forget to each remote peer; 0ms peering timeout = non-blocking warm-up.
   for (const peerOrigin of remoteOrigins) {
-    sendCallRelay(peerOrigin, [event]).catch(err => {
-      console.warn(`[federation] Typing relay to ${peerOrigin} failed:`, err);
-    });
+    sendCallRelay(peerOrigin, [event], { peeringTimeoutMs: 0 })
+      .then(result => {
+        if (!result.ok) {
+          console.debug(`[federation] Typing relay to ${peerOrigin}: ${result.reason} ${result.error}`);
+        }
+      })
+      .catch(err => {
+        console.warn(`[federation] Typing relay to ${peerOrigin} threw unexpectedly:`, err);
+      });
   }
 }

packages/server/src/utils/federationPeering.test.ts

@@ -1,5 +1,6 @@
-import { describe, it, expect } from 'vitest';
+import { describe, it, expect, vi } from 'vitest';
 import type { EnsurePeeredResult } from './federationPeering.js';
+import { racePeering } from './federationPeering.js';
 
 describe('EnsurePeeredResult type', () => {
   it('active result has peerId', () => {
@@ -43,3 +44,71 @@ describe('EnsurePeeredResult type', () => {
     }
   });
 });
+
+describe('racePeering', () => {
+  it('returns the ensurePeered result when it resolves before the timeout', async () => {
+    const stub = vi.fn(async (): Promise<EnsurePeeredResult> => ({
+      status: 'active',
+      peerId: 'peer-1',
+    }));
+    const result = await racePeering('https://example.com', 1_000, stub);
+    expect(result).toEqual({ status: 'active', peerId: 'peer-1' });
+    expect(stub).toHaveBeenCalledWith('https://example.com');
+  });
+
+  it('returns timeout when ensurePeered takes longer than the deadline', async () => {
+    vi.useFakeTimers();
+    const stub = vi.fn((): Promise<EnsurePeeredResult> => new Promise(() => {
+      // Never resolves — simulates a slow handshake.
+    }));
+    const racePromise = racePeering('https://example.com', 50, stub);
+    await vi.advanceTimersByTimeAsync(50);
+    const result = await racePromise;
+    expect(result).toEqual({ status: 'timeout' });
+    vi.useRealTimers();
+  });
+
+  it('returns rejected result verbatim when ensurePeered resolves with rejection', async () => {
+    const stub = vi.fn(async (): Promise<EnsurePeeredResult> => ({
+      status: 'rejected',
+      error: 'peer denied',
+    }));
+    const result = await racePeering('https://example.com', 1_000, stub);
+    expect(result).toEqual({ status: 'rejected', error: 'peer denied' });
+  });
+
+  it('attaches a warn-logged catch to the background handshake when the timeout wins', async () => {
+    vi.useFakeTimers();
+    const warnSpy = vi.spyOn(console, 'warn').mockImplementation(() => {});
+    const stub = vi.fn(() => new Promise<EnsurePeeredResult>((_, reject) => {
+      setTimeout(() => reject(new Error('late failure')), 30);
+    }));
+    const racePromise = racePeering('https://example.com', 10, stub);
+    await vi.advanceTimersByTimeAsync(10);
+    const result = await racePromise;
+    expect(result).toEqual({ status: 'timeout' });
+    await vi.advanceTimersByTimeAsync(30);
+    // Let microtasks flush so the .catch handler runs.
+    await Promise.resolve();
+    expect(warnSpy).toHaveBeenCalledWith(
+      expect.stringContaining('background handshake'),
+      'https://example.com',
+      expect.any(Error),
+    );
+    vi.useRealTimers();
+    warnSpy.mockRestore();
+  });
+
+  it('normalizes a thrown handshake error into { status: failed } without emitting the background warn', async () => {
+    const warnSpy = vi.spyOn(console, 'warn').mockImplementation(() => {});
+    const stub = vi.fn(async (): Promise<EnsurePeeredResult> => {
+      throw new Error('immediate handshake failure');
+    });
+    const result = await racePeering('https://example.com', 1_000, stub);
+    expect(result).toEqual({ status: 'failed', error: 'immediate handshake failure' });
+    // The handshake rejection was the race winner — no background warn should fire.
+    await Promise.resolve();
+    expect(warnSpy).not.toHaveBeenCalled();
+    warnSpy.mockRestore();
+  });
+});

packages/server/src/utils/federationPeering.ts

@@ -210,3 +210,46 @@ async function performHandshake(
 export function _clearInFlightPeering(): void {
   inFlightPeering.clear();
 }
+
+/**
+ * Race ensurePeered() against a deadline. On timeout, the background
+ * handshake is NOT aborted — it continues so the next attempt finds
+ * the peer active. A warn-logged catch is attached so a late-rejecting
+ * background promise does not emit an unhandledRejection.
+ *
+ * The ensurePeered implementation is injectable for testing; the default
+ * is the real function.
+ */
+export async function racePeering(
+  origin: string,
+  timeoutMs: number,
+  ensurePeeredFn: (origin: string) => Promise<EnsurePeeredResult> = ensurePeered,
+): Promise<EnsurePeeredResult | { status: 'timeout' }> {
+  const handshake = ensurePeeredFn(origin);
+
+  let timeoutHandle: ReturnType<typeof setTimeout> | undefined;
+  const timeoutPromise = new Promise<{ status: 'timeout' }>(resolve => {
+    timeoutHandle = setTimeout(() => resolve({ status: 'timeout' }), timeoutMs);
+  });
+
+  let raceResult: EnsurePeeredResult | { status: 'timeout' };
+  try {
+    raceResult = await Promise.race([handshake, timeoutPromise]);
+  } catch (err) {
+    // ensurePeeredFn rejected as the race winner. Normalize to failed.
+    if (timeoutHandle) clearTimeout(timeoutHandle);
+    const message = err instanceof Error ? err.message : 'Unknown handshake error';
+    return { status: 'failed', error: message };
+  }
+  if (timeoutHandle) clearTimeout(timeoutHandle);
+
+  // Only when the timeout arm won is the background handshake still running.
+  // Guard its eventual rejection so we don't emit unhandledRejection.
+  if (raceResult.status === 'timeout') {
+    handshake.catch(err => {
+      console.warn('[federation] background handshake after call-relay race:', origin, err);
+    });
+  }
+
+  return raceResult;
+}

packages/server/src/ws/events.ts

@@ -6,7 +6,8 @@ import { connectionManager } from './handler.js';
 import type { VoiceRoom, DmRoomMeta, SpaceRoomMeta } from './handler.js';
 import { isMember, getChannelSpaceId, isDmMember, hasPermission, computePermissions, PermissionBits } from '../utils/permissions.js';
 import { broadcastDmMessage, getDmMessageWithUser } from '../routes/dm.js';
-import { MAX_MESSAGE_LENGTH, type MessageWithUser, type Attachment, type DmMessageWithUser, type Embed, type Activity, type ActivityType, type ActivityTimestamps, type ActivityAssets, type ServerEvent } from '@backspace/shared';
+import { MAX_MESSAGE_LENGTH, type MessageWithUser, type Attachment, type DmMessageWithUser, type Embed, type Activity, type ActivityType, type ActivityTimestamps, type ActivityAssets, type ServerEvent, type DmCallUndeliverableFailure, type DmCallUndeliverableReason } from '@backspace/shared';
+import type { CallRelayFailureReason } from '../utils/federationOutbox.js';
 import { ACTIVITY_LIMITS } from '@backspace/shared/src/activities.js';
 import { sanitizeUser } from '../utils/sanitize.js';
 import { deleteAttachmentFiles } from '../utils/fileCleanup.js';
@@ -1692,7 +1693,8 @@ function handleDmCallEnd(event: Record<string, unknown>, userId: string): void {
 
 /**
  * Send S2S dm_call_start to all remote instances with DM members.
- * Fire-and-forget — if delivery fails, the call still works locally.
+ * Fire-and-forget per relay, but aggregates per-peer results to surface
+ * undeliverable calls via `dm_call_undeliverable` to the caller.
  */
 async function sendFederatedCallStart(
   dmChannelId: string,
@@ -1746,9 +1748,33 @@ async function sendFederatedCallStart(
       .run();
   }
 
-  // Check LiveKit configuration
-  if (!config.livekit.apiKey || !config.livekit.apiSecret) {
+  // Classify members relative to this instance.
+  const remoteMembers = members.filter(m => {
+    if (!m.homeInstance) return false;
+    const normalized = m.homeInstance.startsWith('http') ? m.homeInstance : `https://${m.homeInstance}`;
+    return normalized !== ourOrigin;
+  });
+  const localNonCallerMembers = members.filter(m => {
+    if (m.userId === callerId) return false;
+    const home = m.homeInstance
+      ? (m.homeInstance.startsWith('http') ? m.homeInstance : `https://${m.homeInstance}`)
+      : ourOrigin;
+    return home === ourOrigin;
+  });
+  const hasConnectedLocalRingee = localNonCallerMembers.some(m =>
+    connectionManager.isUserOnline(m.userId),
+  );
+
+  // ─── LiveKit pre-flight ────────────────────────────────────────────────────
+  if ((!config.livekit.apiKey || !config.livekit.apiSecret) && remoteMembers.length > 0) {
     console.warn('[federation] Cannot start federated call: LiveKit not configured');
+    emitUndeliverableAndMaybeDestroy({
+      callerId,
+      dmChannelId,
+      federatedId,
+      terminal: !hasConnectedLocalRingee,
+      failures: [{ reason: 'livekit_unavailable' }],
+    });
     return;
   }
 
@@ -1793,55 +1819,133 @@ async function sendFederatedCallStart(
     },
   });
 
-  // Identify remote members for targeted relay
-  const remoteMembers = members.filter(m => {
-    if (!m.homeInstance) return false;
-    const normalized = m.homeInstance.startsWith('http') ? m.homeInstance : `https://${m.homeInstance}`;
-    return normalized !== ourOrigin;
-  });
-
   // Group remote members by home instance (targeted peers)
-  const targetedPeers = new Set<string>();
+  const targetedPeers = new Map<string, string[]>();
   for (const m of remoteMembers) {
     const origin = m.homeInstance!.startsWith('http') ? m.homeInstance! : `https://${m.homeInstance!}`;
-    targetedPeers.add(origin);
+    const bucket = targetedPeers.get(origin) ?? [];
+    bucket.push(m.userId);
+    targetedPeers.set(origin, bucket);
   }
 
-  // Query ALL active federation peers for broadcast
-  const allPeers = db.select({ origin: schema.federationPeers.origin })
+  // Single query for all peers — derives both active-peer list and label map
+  const peerRows = db.select({
+    origin: schema.federationPeers.origin,
+    instanceName: schema.federationPeers.instanceName,
+    status: schema.federationPeers.status,
+  })
     .from(schema.federationPeers)
-    .where(eq(schema.federationPeers.status, 'active'))
     .all();
 
-  // Build parallel relay promises
-  const relayPromises: Promise<void>[] = [];
+  const allPeers = peerRows.filter(r => r.status === 'active');
 
-  // Targeted relay: peers with known remote DM members
-  for (const peerOrigin of targetedPeers) {
-    relayPromises.push(
-      sendCallRelay(peerOrigin, [buildRelayEvent()]).then(result => {
-        if (!result.ok) {
-          console.error(`[federation] Failed to send dm_call_start to ${peerOrigin}: ${result.error}`);
-        }
-      })
-    );
+  const peerLabelByOrigin = new Map<string, string>();
+  for (const row of peerRows) {
+    if (row.instanceName) peerLabelByOrigin.set(row.origin, row.instanceName);
   }
 
-  // All-peers broadcast: every other active peer
+  // ─── Targeted relay: fan out in parallel, await results ────────────────────
+  const targetedResults = await Promise.all(
+    Array.from(targetedPeers.keys()).map(async peerOrigin => {
+      const result = await sendCallRelay(peerOrigin, [buildRelayEvent()]);
+      if (result.ok) {
+        return { origin: peerOrigin, ok: true as const };
+      }
+      const reason = mapCallReasonToEventReason(result.reason);
+      console.error(`[federation] dm_call_start to ${peerOrigin} failed (${result.reason}): ${result.error}`);
+      return { origin: peerOrigin, ok: false as const, reason, error: result.error };
+    }),
+  );
+
+  // ─── All-peers broadcast: fire-and-forget; failures NOT surfaced ───────────
   for (const peer of allPeers) {
     if (targetedPeers.has(peer.origin)) continue;
     if (peer.origin === ourOrigin) continue;
-    relayPromises.push(
-      sendCallRelay(peer.origin, [buildRelayEvent()]).then(result => {
-        if (!result.ok) {
-          console.debug(`[federation] All-peers dm_call_start to ${peer.origin}: ${result.error || 'failed'}`);
-        }
-      })
-    );
+    sendCallRelay(peer.origin, [buildRelayEvent()]).then(result => {
+      if (!result.ok) {
+        console.debug(`[federation] All-peers dm_call_start to ${peer.origin}: ${result.reason} ${result.error}`);
+      }
+    }).catch(err => console.warn('[federation] all-peers broadcast threw:', err));
   }
 
-  // Fire all relays in parallel — each has its own 10s timeout
-  await Promise.all(relayPromises);
+  // ─── Aggregate failures → dm_call_undeliverable ───────────────────────────
+  const failedTargeted = targetedResults.filter(
+    (r): r is Extract<typeof r, { ok: false }> => !r.ok,
+  );
+  if (failedTargeted.length === 0) return;
+
+  const anyTargetedSuccess = targetedResults.some(r => r.ok);
+  const plausibleRecipientRemains = anyTargetedSuccess || hasConnectedLocalRingee;
+
+  const failures: DmCallUndeliverableFailure[] = failedTargeted.map(r => {
+    const affectedUserIds = targetedPeers.get(r.origin) ?? [];
+    return {
+      reason: r.reason,
+      peerOrigin: r.origin,
+      peerLabel: peerLabelByOrigin.get(r.origin),
+      affectedUserIds,
+    };
+  });
+
+  emitUndeliverableAndMaybeDestroy({
+    callerId,
+    dmChannelId,
+    federatedId,
+    terminal: !plausibleRecipientRemains,
+    failures,
+  });
+}
+
+/** Map a sendCallRelay reason to the event-surface reason. */
+function mapCallReasonToEventReason(reason: CallRelayFailureReason): DmCallUndeliverableReason {
+  switch (reason) {
+    case 'peer_rejected': return 'peer_rejected';
+    case 'peer_awaiting_approval': return 'peer_awaiting_approval';
+    case 'peer_transient_failure': return 'peer_transient_failure';
+    case 'post_failed': return 'peer_transient_failure'; // 4xx looks transient to users
+  }
+}
+
+/**
+ * Emit dm_call_undeliverable to the caller. If terminal, also destroy the
+ * local ring room (which clears the ringing timer and voice WS binding)
+ * and broadcast dm_call_ended to non-caller DM members, mirroring the
+ * 60s auto-timeout's cleanup semantics (handler.ts:414-424) so any
+ * ringing client (e.g., a Connection WS from another instance) exits
+ * the ring state instead of hanging.
+ *
+ * Guard: if the caller already cancelled mid-race, the room is already
+ * gone — do NOT emit a phantom "could not reach" toast.
+ */
+function emitUndeliverableAndMaybeDestroy(args: {
+  callerId: string;
+  dmChannelId: string;
+  federatedId: string;
+  terminal: boolean;
+  failures: DmCallUndeliverableFailure[];
+}): void {
+  const { callerId, dmChannelId, federatedId, terminal, failures } = args;
+
+  // Caller may have cancelled mid-race. If the room is gone, move on silently.
+  const room = connectionManager.getRoom(dmChannelId);
+  if (!room) return;
+
+  if (terminal) {
+    connectionManager.clearVoiceWs(callerId);
+    connectionManager.destroyRoom(dmChannelId);
+    connectionManager.sendToDmMembers(dmChannelId, {
+      type: 'dm_call_ended',
+      dmChannelId,
+    }, callerId);
+  }
+
+  connectionManager.sendToUser(callerId, {
+    type: 'dm_call_undeliverable',
+    dmChannelId,
+    federatedCallId: federatedId,
+    terminal,
+    failures,
+  });
 }
 
 async function sendFederatedCallAccept(dmChannelId: string, acceptorUserId: string): Promise<void> {

packages/shared/src/types.ts

@@ -358,6 +358,19 @@ export interface Activity {
 
 // ─── WebSocket Event Types ──────────────────────────────────────────────────
 
+export type DmCallUndeliverableReason =
+  | 'peer_rejected'
+  | 'peer_awaiting_approval'
+  | 'peer_transient_failure'
+  | 'livekit_unavailable';
+
+export interface DmCallUndeliverableFailure {
+  reason: DmCallUndeliverableReason;
+  peerOrigin?: string;
+  peerLabel?: string;
+  affectedUserIds?: string[];
+}
+
 // Client → Server Events
 export type ClientEvent =
   | { type: 'auth'; token: string }
@@ -413,6 +426,7 @@ export type ServerEvent =
   | { type: 'dm_call_accepted'; dmChannelId: string | null; federatedCallId?: string }
   | { type: 'dm_call_rejected'; dmChannelId: string }
   | { type: 'dm_call_ended'; dmChannelId: string }
+  | { type: 'dm_call_undeliverable'; dmChannelId: string | null; federatedCallId: string; terminal: boolean; failures: DmCallUndeliverableFailure[] }
   | { type: 'voice_status_update'; userId: string; channelId: string; isMuted: boolean; isDeafened: boolean; isCameraOn: boolean; isScreenSharing: boolean }
   | { type: 'dm_channel_created'; dmChannel: DmChannel }
   | { type: 'dm_channel_closed'; dmChannelId: string }

packages/web/src/hooks/useWebSocket.ts

@@ -114,6 +114,43 @@ function buildWsUrl(origin: string): string {
   return `${protocol}//${url.host}/ws`;
 }
 
+// ─── Call relay helpers ───────────────────────────────────────────────────────
+
+function buildCallUndeliverableToast(
+  failures: Array<{ reason: string; peerOrigin?: string; peerLabel?: string }>,
+  terminal: boolean,
+): string {
+  const primary = failures[0];
+  const labelFor = (f: { peerLabel?: string; peerOrigin?: string }) =>
+    f.peerLabel ?? f.peerOrigin?.replace(/^https?:\/\//, '') ?? 'the remote instance';
+
+  if (!terminal) {
+    const labels = failures.map(labelFor).join(', ');
+    return `Some participants could not be reached: ${labels}.`;
+  }
+
+  if (failures.length > 1) {
+    const labels = failures.map(labelFor).join(', ');
+    return `Could not reach ${failures.length} instances: ${labels}.`;
+  }
+
+  if (!primary) return 'Call could not be placed.';
+
+  const label = labelFor(primary);
+  switch (primary.reason) {
+    case 'peer_rejected':
+      return `Cannot reach ${label} — this instance requires manual peering approval.`;
+    case 'peer_awaiting_approval':
+      return `Waiting for ${label} admin to approve your instance. Calls will work once approved.`;
+    case 'peer_transient_failure':
+      return `Could not reach ${label}. Try again in a moment.`;
+    case 'livekit_unavailable':
+      return 'Voice is not configured on this instance.';
+    default:
+      return `Call to ${label} could not be placed.`;
+  }
+}
+
 // ─── Event handling ───────────────────────────────────────────────────────────
 
 const HOME_ORIGIN = '';
@@ -954,6 +991,26 @@ function handleEvent(origin: string, event: ServerEvent): void {
       break;
     }
 
+    case 'dm_call_undeliverable': {
+      if (!isHome && !activePeerOrigins.has(origin)) break;
+
+      const { setIncomingCall, setOutgoingCall, setActiveDmCall, disconnectFn, clearFederatedCallData } = useVoiceStore.getState();
+      const { addToast } = useUIStore.getState();
+
+      if (event.terminal) {
+        // Tear down local outbound call state — mirrors dm_call_ended.
+        setIncomingCall(null);
+        setOutgoingCall(null);
+        setActiveDmCall(null);
+        clearFederatedCallData();
+        if (disconnectFn) disconnectFn();
+      }
+
+      const msg = buildCallUndeliverableToast(event.failures, event.terminal);
+      addToast(msg, event.terminal ? 'warning' : 'info', 8_000);
+      break;
+    }
+
     // ─── DM channel events (all origins) ────────────────────────────────────
 
     case 'dm_channel_created': {