diff --git a/adapter/experimental.go b/adapter/experimental.go
index 67191141..cd46fb1f 100644
--- a/adapter/experimental.go
+++ b/adapter/experimental.go
@@ -143,6 +143,7 @@ type OutboundGroup interface {
 type URLTestGroup interface {
 	OutboundGroup
 	URLTest(ctx context.Context) (map[string]uint16, error)
+	PerformUpdateCheck()
 }
 
 func OutboundTag(detour Outbound) string {
diff --git a/experimental/clashapi/proxies.go b/experimental/clashapi/proxies.go
index ef88ff37..afd7ba22 100644
--- a/experimental/clashapi/proxies.go
+++ b/experimental/clashapi/proxies.go
@@ -184,6 +184,30 @@ func updateProxy(w http.ResponseWriter, r *http.Request) {
 	render.NoContent(w, r)
 }
 
+func groupContains(outboundManager adapter.OutboundManager, outboundGroup adapter.OutboundGroup, tag string, visited map[string]bool) bool {
+	for _, memberTag := range outboundGroup.All() {
+		if memberTag == tag {
+			return true
+		}
+		member, loaded := outboundManager.Outbound(memberTag)
+		if !loaded {
+			continue
+		}
+		if group.RealTag(member) == tag {
+			return true
+		}
+		memberGroup, isGroup := member.(adapter.OutboundGroup)
+		if !isGroup || visited[memberTag] {
+			continue
+		}
+		visited[memberTag] = true
+		if groupContains(outboundManager, memberGroup, tag, visited) {
+			return true
+		}
+	}
+	return false
+}
+
 func getProxyDelay(server *Server) func(w http.ResponseWriter, r *http.Request) {
 	return func(w http.ResponseWriter, r *http.Request) {
 		query := r.URL.Query()
@@ -213,6 +237,16 @@ func getProxyDelay(server *Server) func(w http.ResponseWriter, r *http.Request)
 					Delay: delay,
 				})
 			}
+			for _, detour := range server.outbound.Outbounds() {
+				urlTestGroup, isURLTestGroup := detour.(adapter.URLTestGroup)
+				if !isURLTestGroup {
+					continue
+				}
+				if !groupContains(server.outbound, urlTestGroup, realTag, map[string]bool{detour.Tag(): true}) {
+					continue
+				}
+				urlTestGroup.PerformUpdateCheck()
+			}
 		}()
 
 		if ctx.Err() != nil {
diff --git a/go.mod b/go.mod
index 6f8e242e..10362e4d 100644
--- a/go.mod
+++ b/go.mod
@@ -34,7 +34,7 @@ require (
 	github.com/sagernet/gomobile v0.1.12
 	github.com/sagernet/gvisor v0.0.0-20250811.0-sing-box-mod.1
 	github.com/sagernet/quic-go v0.59.0-sing-box-mod.4
-	github.com/sagernet/sing v0.8.13
+	github.com/sagernet/sing v0.8.14
 	github.com/sagernet/sing-mux v0.3.5
 	github.com/sagernet/sing-quic v0.6.4-0.20260803041914-d83826c306d7
 	github.com/sagernet/sing-shadowsocks v0.2.8
diff --git a/go.sum b/go.sum
index 6ab540be..53ebbc08 100644
--- a/go.sum
+++ b/go.sum
@@ -236,8 +236,8 @@ github.com/sagernet/nftables v0.3.0-mod.2 h1:ck2KMU02OxL1eDFgGaWYglMDpoOZ7OHzxje
 github.com/sagernet/nftables v0.3.0-mod.2/go.mod h1:8kslHG4VvYNihcco+i6uxIX7qbT8A56T0y5q7U44ZaQ=
 github.com/sagernet/quic-go v0.59.0-sing-box-mod.4 h1:6qvrUW79S+CrPwWz6cMePXohgjHoKxLo3c+MDhNwc3o=
 github.com/sagernet/quic-go v0.59.0-sing-box-mod.4/go.mod h1:OqILvS182CyOol5zNNo6bguvOGgXzV459+chpRaUC+4=
-github.com/sagernet/sing v0.8.13 h1:yVoXnx9nPxfjlwD4Tp+Wd9zuW2tfiSVrcRDBZNbKRCw=
-github.com/sagernet/sing v0.8.13/go.mod h1:olXxWQNqRW/l2Q6JI3b2Qmz8iQnIFlOeeH8bx6JhgUA=
+github.com/sagernet/sing v0.8.14 h1:S6Netv4F61uNAuD/sUbHnGuNUEPwtL08Ouk0//CVYgM=
+github.com/sagernet/sing v0.8.14/go.mod h1:olXxWQNqRW/l2Q6JI3b2Qmz8iQnIFlOeeH8bx6JhgUA=
 github.com/sagernet/sing-mux v0.3.5 h1:RHnhVEc+SFqkrK4xMygYjDwwLhzp2Bj3lztSukONfhI=
 github.com/sagernet/sing-mux v0.3.5/go.mod h1:QvlKMyNBNrQoyX4x+gq028uPbLM2XeRpWtDsWBJbFSk=
 github.com/sagernet/sing-quic v0.6.4-0.20260803041914-d83826c306d7 h1:D46kmyvKMNVFvL3KXdq3T4vy8r29xCMmSqNuQHJBybE=
diff --git a/protocol/group/urltest.go b/protocol/group/urltest.go
index 730040f7..cf82c342 100644
--- a/protocol/group/urltest.go
+++ b/protocol/group/urltest.go
@@ -115,6 +115,10 @@ func (s *URLTest) CheckOutbounds() {
 	s.group.CheckOutbounds(true)
 }
 
+func (s *URLTest) PerformUpdateCheck() {
+	s.group.performUpdateCheck()
+}
+
 func (s *URLTest) DialContext(ctx context.Context, network string, destination M.Socksaddr) (net.Conn, error) {
 	s.group.Touch()
 	var outbound adapter.Outbound
@@ -202,6 +206,7 @@ type URLTestGroup struct {
 	interruptGroup               *interrupt.Group
 	interruptExternalConnections bool
 	access                       sync.Mutex
+	updateAccess                 sync.Mutex
 	ticker                       *time.Ticker
 	close                        chan struct{}
 	started                      bool
@@ -362,6 +367,11 @@ func (g *URLTestGroup) URLTest(ctx context.Context) (map[string]uint16, error) {
 	return g.urlTest(ctx, false)
 }
 
+type urlTestResult struct {
+	delay uint16
+	err   error
+}
+
 func (g *URLTestGroup) urlTest(ctx context.Context, force bool) (map[string]uint16, error) {
 	result := make(map[string]uint16)
 	if g.checking.Swap(true) {
@@ -389,18 +399,28 @@ func (g *URLTestGroup) urlTest(ctx context.Context, force bool) (map[string]uint
 		b.Go(realTag, func() (any, error) {
 			testCtx, cancel := context.WithTimeout(g.ctx, C.TCPTimeout)
 			defer cancel()
-			t, err := urltest.URLTest(testCtx, g.link, p)
-			if err != nil {
-				g.logger.Debug("outbound ", tag, " unavailable: ", err)
+			testChan := make(chan urlTestResult, 1)
+			go func() {
+				delay, testErr := urltest.URLTest(testCtx, g.link, p)
+				testChan <- urlTestResult{delay, testErr}
+			}()
+			var testResult urlTestResult
+			select {
+			case testResult = <-testChan:
+			case <-testCtx.Done():
+				testResult.err = testCtx.Err()
+			}
+			if testResult.err != nil {
+				g.logger.Debug("outbound ", tag, " unavailable: ", testResult.err)
 				g.history.DeleteURLTestHistory(realTag)
 			} else {
-				g.logger.Debug("outbound ", tag, " available: ", t, "ms")
+				g.logger.Debug("outbound ", tag, " available: ", testResult.delay, "ms")
 				g.history.StoreURLTestHistory(realTag, &adapter.URLTestHistory{
 					Time:  time.Now(),
-					Delay: t,
+					Delay: testResult.delay,
 				})
 				resultAccess.Lock()
-				result[tag] = t
+				result[tag] = testResult.delay
 				resultAccess.Unlock()
 			}
 			return nil, nil
@@ -412,6 +432,8 @@ func (g *URLTestGroup) urlTest(ctx context.Context, force bool) (map[string]uint
 }
 
 func (g *URLTestGroup) performUpdateCheck() {
+	g.updateAccess.Lock()
+	defer g.updateAccess.Unlock()
 	var updated bool
 	if outbound, exists := g.Select(N.NetworkTCP); outbound != nil && (g.selectedOutboundTCP == nil || (exists && outbound != g.selectedOutboundTCP)) {
 		if g.selectedOutboundTCP != nil {
diff --git a/protocol/ssh/outbound.go b/protocol/ssh/outbound.go
index b76c79ad..7d7bd7dd 100644
--- a/protocol/ssh/outbound.go
+++ b/protocol/ssh/outbound.go
@@ -35,7 +35,6 @@ var _ adapter.InterfaceUpdateListener = (*Outbound)(nil)
 
 type Outbound struct {
 	outbound.Adapter
-	ctx               context.Context
 	logger            logger.ContextLogger
 	dialer            N.Dialer
 	serverAddr        M.Socksaddr
@@ -56,7 +55,6 @@ func NewOutbound(ctx context.Context, router adapter.Router, logger log.ContextL
 	}
 	outbound := &Outbound{
 		Adapter:           outbound.NewAdapterWithDialerOptions(C.TypeSSH, tag, []string{N.NetworkTCP}, options.DialerOptions),
-		ctx:               ctx,
 		logger:            logger,
 		dialer:            outboundDialer,
 		serverAddr:        options.ServerOptions.Build(),
@@ -121,7 +119,7 @@ func randomVersion() string {
 	return version
 }
 
-func (s *Outbound) connect() (*ssh.Client, error) {
+func (s *Outbound) connect(ctx context.Context) (client *ssh.Client, err error) {
 	if s.client != nil {
 		return s.client, nil
 	}
@@ -133,10 +131,24 @@ func (s *Outbound) connect() (*ssh.Client, error) {
 		return s.client, nil
 	}
 
-	conn, err := s.dialer.DialContext(s.ctx, N.NetworkTCP, s.serverAddr)
+	conn, err := s.dialer.DialContext(ctx, N.NetworkTCP, s.serverAddr)
 	if err != nil {
 		return nil, err
 	}
+	if ctx.Done() != nil {
+		handshakeConn := conn
+		stopContext := context.AfterFunc(ctx, func() {
+			_ = handshakeConn.Close()
+		})
+		defer func() {
+			if !stopContext() {
+				s.client = nil
+				s.clientConn = nil
+				client = nil
+				err = ctx.Err()
+			}
+		}()
+	}
 	config := &ssh.ClientConfig{
 		User:              s.user,
 		Auth:              s.authMethod,
@@ -161,7 +173,7 @@ func (s *Outbound) connect() (*ssh.Client, error) {
 		return nil, E.Cause(err, "connect to ssh server")
 	}
 
-	client := ssh.NewClient(clientConn, chans, reqs)
+	client = ssh.NewClient(clientConn, chans, reqs)
 
 	s.clientConn = conn
 	s.client = client
@@ -187,7 +199,7 @@ func (s *Outbound) Close() error {
 }
 
 func (s *Outbound) DialContext(ctx context.Context, network string, destination M.Socksaddr) (net.Conn, error) {
-	client, err := s.connect()
+	client, err := s.connect(ctx)
 	if err != nil {
 		return nil, err
 	}