diff --git a/agent/claudecode/session.go b/agent/claudecode/session.go
index 8badc68..d8d4f3c 100644
--- a/agent/claudecode/session.go
+++ b/agent/claudecode/session.go
@@ -466,8 +466,18 @@ func (cs *claudeSession) Alive() bool {
 
 func (cs *claudeSession) Close() error {
 	cs.cancel()
-	<-cs.done
-	return nil
+
+	select {
+	case <-cs.done:
+		return nil
+	case <-time.After(8 * time.Second):
+		slog.Warn("claudeSession: graceful close timed out, killing process")
+		if cs.cmd != nil && cs.cmd.Process != nil {
+			_ = cs.cmd.Process.Kill()
+		}
+		<-cs.done
+		return nil
+	}
 }
 
 // filterEnv returns a copy of env with entries matching the given key removed.
diff --git a/agent/codex/session.go b/agent/codex/session.go
index 31ec3ac..0bae967 100644
--- a/agent/codex/session.go
+++ b/agent/codex/session.go
@@ -13,6 +13,7 @@ import (
 	"strings"
 	"sync"
 	"sync/atomic"
+	"time"
 	"unicode/utf8"
 
 	"github.com/chenhg5/cc-connect/core"
@@ -291,7 +292,16 @@ func (cs *codexSession) Alive() bool {
 func (cs *codexSession) Close() error {
 	cs.alive.Store(false)
 	cs.cancel()
-	cs.wg.Wait()
+	done := make(chan struct{})
+	go func() {
+		cs.wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(8 * time.Second):
+		slog.Warn("codexSession: close timed out, abandoning wg.Wait")
+	}
 	close(cs.events)
 	return nil
 }
diff --git a/agent/cursor/session.go b/agent/cursor/session.go
index e844e8b..9ae13d3 100644
--- a/agent/cursor/session.go
+++ b/agent/cursor/session.go
@@ -13,6 +13,7 @@ import (
 	"strings"
 	"sync"
 	"sync/atomic"
+	"time"
 	"unicode/utf8"
 
 	"github.com/chenhg5/cc-connect/core"
@@ -382,7 +383,16 @@ func (cs *cursorSession) Alive() bool {
 func (cs *cursorSession) Close() error {
 	cs.alive.Store(false)
 	cs.cancel()
-	cs.wg.Wait()
+	done := make(chan struct{})
+	go func() {
+		cs.wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(8 * time.Second):
+		slog.Warn("cursorSession: close timed out, abandoning wg.Wait")
+	}
 	close(cs.events)
 	return nil
 }
diff --git a/agent/gemini/session.go b/agent/gemini/session.go
index 086b8e9..498a43d 100644
--- a/agent/gemini/session.go
+++ b/agent/gemini/session.go
@@ -13,6 +13,7 @@ import (
 	"strings"
 	"sync"
 	"sync/atomic"
+	"time"
 	"unicode/utf8"
 
 	"github.com/chenhg5/cc-connect/core"
@@ -370,7 +371,16 @@ func (gs *geminiSession) Alive() bool {
 func (gs *geminiSession) Close() error {
 	gs.alive.Store(false)
 	gs.cancel()
-	gs.wg.Wait()
+	done := make(chan struct{})
+	go func() {
+		gs.wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(8 * time.Second):
+		slog.Warn("geminiSession: close timed out, abandoning wg.Wait")
+	}
 	close(gs.events)
 	return nil
 }
diff --git a/agent/opencode/session.go b/agent/opencode/session.go
index 16be023..31d354e 100644
--- a/agent/opencode/session.go
+++ b/agent/opencode/session.go
@@ -12,6 +12,7 @@ import (
 	"os/exec"
 	"sync"
 	"sync/atomic"
+	"time"
 	"unicode/utf8"
 
 	"github.com/chenhg5/cc-connect/core"
@@ -305,7 +306,16 @@ func (s *opencodeSession) Alive() bool {
 func (s *opencodeSession) Close() error {
 	s.alive.Store(false)
 	s.cancel()
-	s.wg.Wait()
+	done := make(chan struct{})
+	go func() {
+		s.wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(8 * time.Second):
+		slog.Warn("opencodeSession: close timed out, abandoning wg.Wait")
+	}
 	close(s.events)
 	return nil
 }
diff --git a/agent/qoder/session.go b/agent/qoder/session.go
index 0e3beda..619b6ff 100644
--- a/agent/qoder/session.go
+++ b/agent/qoder/session.go
@@ -13,6 +13,7 @@ import (
 	"strings"
 	"sync"
 	"sync/atomic"
+	"time"
 	"unicode/utf8"
 
 	"github.com/chenhg5/cc-connect/core"
@@ -276,7 +277,16 @@ func (qs *qoderSession) Alive() bool {
 func (qs *qoderSession) Close() error {
 	qs.alive.Store(false)
 	qs.cancel()
-	qs.wg.Wait()
+	done := make(chan struct{})
+	go func() {
+		qs.wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(8 * time.Second):
+		slog.Warn("qoderSession: close timed out, abandoning wg.Wait")
+	}
 	close(qs.events)
 	return nil
 }
diff --git a/core/engine.go b/core/engine.go
index 1e165f1..875419c 100644
--- a/core/engine.go
+++ b/core/engine.go
@@ -253,14 +253,20 @@ func (e *Engine) Stop() error {
 	e.cancel()
 
 	e.interactiveMu.Lock()
-	for key, state := range e.interactiveStates {
-		if state.agentSession != nil {
-			state.agentSession.Close()
-		}
-		delete(e.interactiveStates, key)
+	states := make(map[string]*interactiveState, len(e.interactiveStates))
+	for k, v := range e.interactiveStates {
+		states[k] = v
+		delete(e.interactiveStates, k)
 	}
 	e.interactiveMu.Unlock()
 
+	for key, state := range states {
+		if state.agentSession != nil {
+			slog.Debug("engine.Stop: closing agent session", "session", key)
+			state.agentSession.Close()
+		}
+	}
+
 	var errs []error
 	for _, p := range e.platforms {
 		if err := p.Stop(); err != nil {
@@ -561,17 +567,29 @@ func (e *Engine) getOrCreateInteractiveState(sessionKey string, p Platform, repl
 
 func (e *Engine) cleanupInteractiveState(sessionKey string) {
 	e.interactiveMu.Lock()
-	defer e.interactiveMu.Unlock()
-
 	state, ok := e.interactiveStates[sessionKey]
-	if ok && state.agentSession != nil {
+	delete(e.interactiveStates, sessionKey)
+	e.interactiveMu.Unlock()
+
+	if ok && state != nil && state.agentSession != nil {
+		slog.Debug("cleanupInteractiveState: closing agent session", "session", sessionKey)
 		closeStart := time.Now()
-		state.agentSession.Close()
-		if elapsed := time.Since(closeStart); elapsed >= slowAgentClose {
-			slog.Warn("slow agent session close", "elapsed", elapsed, "session", sessionKey)
+
+		done := make(chan struct{})
+		go func() {
+			state.agentSession.Close()
+			close(done)
+		}()
+
+		select {
+		case <-done:
+			if elapsed := time.Since(closeStart); elapsed >= slowAgentClose {
+				slog.Warn("slow agent session close", "elapsed", elapsed, "session", sessionKey)
+			}
+		case <-time.After(10 * time.Second):
+			slog.Error("agent session close timed out (10s), abandoning", "session", sessionKey)
 		}
 	}
-	delete(e.interactiveStates, sessionKey)
 }
 
 func (e *Engine) processInteractiveEvents(state *interactiveState, session *Session, sessionKey string, turnStart time.Time) {
@@ -803,7 +821,9 @@ func (e *Engine) handleCommand(p Platform, msg *Message, raw string) bool {
 }
 
 func (e *Engine) cmdNew(p Platform, msg *Message, args []string) {
+	slog.Info("cmdNew: cleaning up old session", "session_key", msg.SessionKey)
 	e.cleanupInteractiveState(msg.SessionKey)
+	slog.Info("cmdNew: cleanup done, creating new session", "session_key", msg.SessionKey)
 	name := "session"
 	if len(args) > 0 {
 		name = strings.Join(args, " ")
@@ -866,6 +886,7 @@ func (e *Engine) cmdSwitch(p Platform, msg *Message, args []string) {
 	}
 	prefix := strings.TrimSpace(args[0])
 
+	slog.Info("cmdSwitch: listing agent sessions", "session_key", msg.SessionKey)
 	agentSessions, err := e.agent.ListSessions(e.ctx)
 	if err != nil {
 		e.reply(p, msg.ReplyCtx, fmt.Sprintf("❌ %v", err))
@@ -884,7 +905,9 @@ func (e *Engine) cmdSwitch(p Platform, msg *Message, args []string) {
 		return
 	}
 
+	slog.Info("cmdSwitch: cleaning up old session", "session_key", msg.SessionKey)
 	e.cleanupInteractiveState(msg.SessionKey)
+	slog.Info("cmdSwitch: cleanup done", "session_key", msg.SessionKey)
 
 	session := e.sessions.GetOrCreateActive(msg.SessionKey)
 	session.AgentSessionID = matched.ID