diff --git a/src/core/bot.ts b/src/core/bot.ts
index 0955937..0e1db40 100644
--- a/src/core/bot.ts
+++ b/src/core/bot.ts
@@ -221,6 +221,32 @@ export class LettaBot implements AgentSession {
     }
   }
 
+  private getSessionTimeoutMs(): number {
+    const envTimeoutMs = Number(process.env.LETTA_SESSION_TIMEOUT_MS);
+    if (Number.isFinite(envTimeoutMs) && envTimeoutMs > 0) {
+      return envTimeoutMs;
+    }
+    return 60000;
+  }
+
+  private async withSessionTimeout<T>(
+    promise: Promise<T>,
+    label: string,
+  ): Promise<T> {
+    const timeoutMs = this.getSessionTimeoutMs();
+    let timeoutId: ReturnType<typeof setTimeout> | undefined;
+    const timeoutPromise = new Promise<T>((_, reject) => {
+      timeoutId = setTimeout(() => {
+        reject(new Error(`${label} timed out after ${timeoutMs}ms`));
+      }, timeoutMs);
+    });
+    try {
+      return await Promise.race([promise, timeoutPromise]);
+    } finally {
+      if (timeoutId) clearTimeout(timeoutId);
+    }
+  }
+
   private baseSessionOptions(canUseTool?: CanUseToolCallback) {
     return {
       permissionMode: 'bypassPermissions' as const,
@@ -387,10 +413,16 @@ export class LettaBot implements AgentSession {
 
     // Initialize eagerly so the subprocess is ready before the first send()
     console.log(`[Bot] Initializing session subprocess (key=${key})...`);
-    await session.initialize();
-    console.log(`[Bot] Session subprocess ready (key=${key})`);
-    this.sessions.set(key, session);
-    return session;
+    try {
+      await this.withSessionTimeout(session.initialize(), `Session initialize (key=${key})`);
+      console.log(`[Bot] Session subprocess ready (key=${key})`);
+      this.sessions.set(key, session);
+      return session;
+    } catch (error) {
+      // Close immediately so failed initialization cannot leak a subprocess.
+      session.close();
+      throw error;
+    }
   }
 
   /** Legacy convenience: resolve key from shared/per-channel mode and delegate. */
@@ -489,7 +521,7 @@ export class LettaBot implements AgentSession {
 
     // Send message with fallback chain
     try {
-      await session.send(message);
+      await this.withSessionTimeout(session.send(message), `Session send (key=${convKey})`);
     } catch (error) {
       // 409 CONFLICT from orphaned approval
       if (!retried && isApprovalConflictError(error) && this.store.agentId && convId) {
@@ -519,7 +551,12 @@ export class LettaBot implements AgentSession {
           this.store.conversationId = null;
         }
         session = await this.ensureSessionForKey(convKey);
-        await session.send(message);
+        try {
+          await this.withSessionTimeout(session.send(message), `Session send retry (key=${convKey})`);
+        } catch (retryError) {
+          this.invalidateSession(convKey);
+          throw retryError;
+        }
       } else {
         // Unknown error -- invalidate so we get a fresh subprocess next time
         this.invalidateSession(convKey);
@@ -546,11 +583,13 @@ export class LettaBot implements AgentSession {
           if (id) seenToolCallIds.add(id);
         }
 
-        yield msg;
-
-        // Persist state on result
         if (msg.type === 'result') {
           self.persistSessionState(session, capturedConvKey);
+        }
+
+        yield msg;
+
+        if (msg.type === 'result') {
           break;
         }
       }
diff --git a/src/core/sdk-session-contract.test.ts b/src/core/sdk-session-contract.test.ts
index 7231737..4c949b3 100644
--- a/src/core/sdk-session-contract.test.ts
+++ b/src/core/sdk-session-contract.test.ts
@@ -19,16 +19,19 @@ describe('SDK session contract', () => {
   let originalDataDir: string | undefined;
   let originalAgentId: string | undefined;
   let originalRailwayMount: string | undefined;
+  let originalSessionTimeout: string | undefined;
 
   beforeEach(() => {
     dataDir = mkdtempSync(join(tmpdir(), 'lettabot-sdk-contract-'));
     originalDataDir = process.env.DATA_DIR;
     originalAgentId = process.env.LETTA_AGENT_ID;
     originalRailwayMount = process.env.RAILWAY_VOLUME_MOUNT_PATH;
+    originalSessionTimeout = process.env.LETTA_SESSION_TIMEOUT_MS;
 
     process.env.DATA_DIR = dataDir;
     process.env.LETTA_AGENT_ID = 'agent-contract-test';
     delete process.env.RAILWAY_VOLUME_MOUNT_PATH;
+    delete process.env.LETTA_SESSION_TIMEOUT_MS;
 
     vi.clearAllMocks();
   });
@@ -43,6 +46,9 @@ describe('SDK session contract', () => {
     if (originalRailwayMount === undefined) delete process.env.RAILWAY_VOLUME_MOUNT_PATH;
     else process.env.RAILWAY_VOLUME_MOUNT_PATH = originalRailwayMount;
 
+    if (originalSessionTimeout === undefined) delete process.env.LETTA_SESSION_TIMEOUT_MS;
+    else process.env.LETTA_SESSION_TIMEOUT_MS = originalSessionTimeout;
+
     rmSync(dataDir, { recursive: true, force: true });
   });
 
@@ -80,4 +86,82 @@ describe('SDK session contract', () => {
     expect(mockSession.send).toHaveBeenNthCalledWith(2, 'second message');
     expect(mockSession.stream).toHaveBeenCalledTimes(2);
   });
+
+  it('closes session if initialize times out before first send', async () => {
+    process.env.LETTA_SESSION_TIMEOUT_MS = '5';
+
+    const mockSession = {
+      initialize: vi.fn(() => new Promise<never>(() => {})),
+      send: vi.fn(async (_message: unknown) => undefined),
+      stream: vi.fn(() =>
+        (async function* () {
+          yield { type: 'result', success: true };
+        })()
+      ),
+      close: vi.fn(() => undefined),
+      agentId: 'agent-contract-test',
+      conversationId: 'conversation-contract-test',
+    };
+
+    vi.mocked(createSession).mockReturnValue(mockSession as never);
+    vi.mocked(resumeSession).mockReturnValue(mockSession as never);
+
+    const bot = new LettaBot({
+      workingDir: join(dataDir, 'working'),
+      allowedTools: [],
+    });
+
+    await expect(bot.sendToAgent('will timeout')).rejects.toThrow('Session initialize (key=shared) timed out after 5ms');
+    expect(mockSession.close).toHaveBeenCalledTimes(1);
+  });
+
+  it('invalidates retry session when fallback send fails after conversation-missing error', async () => {
+    const missingConversation = new Error('conversation not found');
+    const retryFailure = new Error('network down');
+
+    const firstSession = {
+      initialize: vi.fn(async () => undefined),
+      send: vi.fn(async () => {
+        throw missingConversation;
+      }),
+      stream: vi.fn(() =>
+        (async function* () {
+          yield { type: 'result', success: true };
+        })()
+      ),
+      close: vi.fn(() => undefined),
+      agentId: 'agent-contract-test',
+      conversationId: 'conversation-contract-test-1',
+    };
+
+    const secondSession = {
+      initialize: vi.fn(async () => undefined),
+      send: vi.fn(async () => {
+        throw retryFailure;
+      }),
+      stream: vi.fn(() =>
+        (async function* () {
+          yield { type: 'result', success: true };
+        })()
+      ),
+      close: vi.fn(() => undefined),
+      agentId: 'agent-contract-test',
+      conversationId: 'conversation-contract-test-2',
+    };
+
+    vi.mocked(createSession)
+      .mockReturnValueOnce(firstSession as never)
+      .mockReturnValueOnce(secondSession as never);
+    vi.mocked(resumeSession).mockReturnValue(firstSession as never);
+
+    const bot = new LettaBot({
+      workingDir: join(dataDir, 'working'),
+      allowedTools: [],
+    });
+
+    await expect(bot.sendToAgent('trigger fallback')).rejects.toThrow('network down');
+    expect(firstSession.close).toHaveBeenCalledTimes(1);
+    expect(secondSession.close).toHaveBeenCalledTimes(1);
+    expect(vi.mocked(createSession)).toHaveBeenCalledTimes(2);
+  });
 });