diff --git a/packages/server/src/index.ts b/packages/server/src/index.ts
index 511c3c41..9a50d082 100644
--- a/packages/server/src/index.ts
+++ b/packages/server/src/index.ts
@@ -26,6 +26,7 @@ import { adminRoutes } from './routes/admin.js';
 import { gifRoutes } from './routes/gif.js';
 import { federationRoutes } from './routes/federation.js';
 import { startFederationWorkers, stopFederationWorkers } from './utils/federationWorker.js';
+import './utils/federationRollback.js'; // Side-effect: registers rollback callbacks for outbox terminal failures.
 import { registerCallRelayHooks } from './ws/events.js';
 
 import { registerWebSocket } from './ws/handler.js';
diff --git a/packages/server/src/utils/federationRollback.friendRequest.test.ts b/packages/server/src/utils/federationRollback.friendRequest.test.ts
new file mode 100644
index 00000000..6ef90dbc
--- /dev/null
+++ b/packages/server/src/utils/federationRollback.friendRequest.test.ts
@@ -0,0 +1,107 @@
+import { describe, it, expect, beforeEach, vi } from 'vitest';
+import Database from 'better-sqlite3';
+import { drizzle } from 'drizzle-orm/better-sqlite3';
+import { eq } from 'drizzle-orm';
+import fs from 'node:fs';
+import path from 'node:path';
+import { fileURLToPath } from 'node:url';
+import * as schema from '../db/schema.js';
+import { setWorkerId } from '../utils/snowflake.js';
+
+setWorkerId(1);
+const __dirname = path.dirname(fileURLToPath(import.meta.url));
+
+let sqlite: Database.Database;
+let testDb: ReturnType<typeof drizzle<typeof schema>>;
+const sendToUser = vi.fn();
+
+vi.mock('../db/index.js', () => ({
+  getDb: () => testDb,
+  getRawDb: () => sqlite,
+  schema,
+}));
+
+vi.mock('../ws/handler.js', () => ({
+  connectionManager: { sendToUser },
+}));
+
+function applyMigrations(db: Database.Database): void {
+  const dir = path.resolve(__dirname, '../../drizzle');
+  for (const f of fs.readdirSync(dir).filter(f => f.endsWith('.sql')).sort()) {
+    const sqlText = fs.readFileSync(path.join(dir, f), 'utf8');
+    for (const stmt of sqlText.split(/-->\s*statement-breakpoint/)) {
+      const clean = stmt.trim();
+      if (clean) db.exec(clean);
+    }
+  }
+}
+
+beforeEach(() => {
+  sqlite = new Database(':memory:');
+  testDb = drizzle(sqlite, { schema });
+  applyMigrations(sqlite);
+  sendToUser.mockReset();
+});
+
+describe('rollbackFriendRequestCreate', () => {
+  it('deletes the matching friend_requests row and emits friend_request_relay_failed to sender', async () => {
+    testDb.insert(schema.users).values([
+      { id: 'sender', username: 'bob', passwordHash: 'x', status: 'offline', isAdmin: 0, createdAt: Date.now() },
+      { id: 'stub', username: 'alice@orbit.test', passwordHash: '!federation-replicated',
+        status: 'offline', isAdmin: 0, homeInstance: 'orbit.test', homeUserId: 'remote-1', createdAt: Date.now() },
+    ] as typeof schema.users.$inferInsert[]).run();
+
+    testDb.insert(schema.friendRequests).values({
+      id: 'req-1',
+      fromId: 'sender',
+      toId: 'stub',
+      status: 'pending',
+      createdAt: Date.now(),
+      relayMessageId: 'friend_req:remote-1:sender:1234',
+    } as typeof schema.friendRequests.$inferInsert).run();
+
+    const { rollbackFriendRequestCreate } = await import('./federationRollback.js');
+    rollbackFriendRequestCreate('friend_req:remote-1:sender:1234', 'recipient_not_found');
+
+    const remaining = testDb.select().from(schema.friendRequests).where(eq(schema.friendRequests.id, 'req-1')).get();
+    expect(remaining).toBeUndefined();
+
+    expect(sendToUser).toHaveBeenCalledOnce();
+    const [userId, event] = sendToUser.mock.calls[0]!;
+    expect(userId).toBe('sender');
+    expect(event.type).toBe('friend_request_relay_failed');
+    expect(event.requestId).toBe('req-1');
+    expect(event.reason).toBe('user_not_found');
+    expect(event.targetHandle).toBe('alice@orbit.test');
+    expect(typeof event.message).toBe('string');
+  });
+
+  it('is idempotent: no-op if no row matches the messageId', async () => {
+    const { rollbackFriendRequestCreate } = await import('./federationRollback.js');
+    expect(() => rollbackFriendRequestCreate('no-such-msg', 'recipient_not_found')).not.toThrow();
+    expect(sendToUser).not.toHaveBeenCalled();
+  });
+
+  it('maps unknown reasons to peer_rejected', async () => {
+    testDb.insert(schema.users).values([
+      { id: 'sender', username: 'bob', passwordHash: 'x', status: 'offline', isAdmin: 0, createdAt: Date.now() },
+      { id: 'stub', username: 'alice@orbit.test', passwordHash: '!federation-replicated',
+        status: 'offline', isAdmin: 0, homeInstance: 'orbit.test', homeUserId: 'remote-1', createdAt: Date.now() },
+    ] as typeof schema.users.$inferInsert[]).run();
+    testDb.insert(schema.friendRequests).values({
+      id: 'req-2',
+      fromId: 'sender',
+      toId: 'stub',
+      status: 'pending',
+      createdAt: Date.now(),
+      relayMessageId: 'msg-x',
+    } as typeof schema.friendRequests.$inferInsert).run();
+
+    const { rollbackFriendRequestCreate } = await import('./federationRollback.js');
+    rollbackFriendRequestCreate('msg-x', 'attribution_mismatch');
+
+    expect(sendToUser).toHaveBeenCalledOnce();
+    const event = sendToUser.mock.calls[0]![1];
+    expect(event.reason).toBe('peer_rejected');
+  });
+});
diff --git a/packages/server/src/utils/federationRollback.ts b/packages/server/src/utils/federationRollback.ts
index 8512e3d0..c011c6db 100644
--- a/packages/server/src/utils/federationRollback.ts
+++ b/packages/server/src/utils/federationRollback.ts
@@ -12,6 +12,11 @@
  * Errors thrown by callbacks are logged but not re-thrown — rollback failure
  * must not prevent the outbox entry from being deleted.
  */
+import { getDb } from '../db/index.js';
+import * as schema from '../db/schema.js';
+import { eq } from 'drizzle-orm';
+import { connectionManager } from '../ws/handler.js';
+
 type PermanentFailureCallback = (messageId: string, reason: string) => void;
 
 const callbacks = new Map<string, PermanentFailureCallback>();
@@ -37,3 +42,54 @@ export function invokePermanentFailureCallback(eventType: string, messageId: str
 export function _resetCallbacks(): void {
   callbacks.clear();
 }
+
+/**
+ * Rollback handler for 'friend_request_create' outbox events.
+ *
+ * Deletes the pending friend request row whose relayMessageId matches the
+ * failed outbox message, then notifies the sender via WebSocket so the client
+ * can surface an appropriate error toast.
+ */
+export function rollbackFriendRequestCreate(messageId: string, receiverReason: string): void {
+  const db = getDb();
+
+  const row = db
+    .select()
+    .from(schema.friendRequests)
+    .where(eq(schema.friendRequests.relayMessageId, messageId))
+    .get();
+
+  if (!row) return; // Idempotent — no row to roll back.
+
+  // Look up recipient handle for the toast text BEFORE deleting.
+  const recipient = db
+    .select({ username: schema.users.username })
+    .from(schema.users)
+    .where(eq(schema.users.id, row.toId))
+    .get();
+  const targetHandle = recipient?.username ?? 'unknown';
+
+  db.delete(schema.friendRequests).where(eq(schema.friendRequests.id, row.id)).run();
+
+  // Reason mapping: receiver-side reason → client-facing reason.
+  //   'recipient_not_found' → 'user_not_found' (the looked-up identity vanished)
+  //   anything else         → 'peer_rejected' (catch-all)
+  const reason: 'user_not_found' | 'peer_rejected' =
+    receiverReason === 'recipient_not_found' ? 'user_not_found' : 'peer_rejected';
+
+  const message =
+    reason === 'user_not_found'
+      ? `User ${targetHandle} no longer exists on the remote instance.`
+      : `Friend request to ${targetHandle} was rejected by the remote instance.`;
+
+  connectionManager.sendToUser(row.fromId, {
+    type: 'friend_request_relay_failed',
+    requestId: row.id,
+    reason,
+    message,
+    targetHandle,
+  });
+}
+
+// Register the callback at module-load time so the worker invokes it.
+registerPermanentFailureCallback('friend_request_create', rollbackFriendRequestCreate);