diff --git a/internal/dns/loop.go b/internal/dns/loop.go
index eae0ac7c..99aeb346 100644
--- a/internal/dns/loop.go
+++ b/internal/dns/loop.go
@@ -38,10 +38,12 @@ func NewLooper(conf Configurator, settings settings.DNS, logger logging.Logger,
 	}
 }
 
-func (l *looper) attemptingRestart(err error) {
+func (l *looper) logAndWait(ctx context.Context, err error) {
 	l.logger.Warn(err)
 	l.logger.Info("attempting restart in 10 seconds")
-	time.Sleep(10 * time.Second)
+	ctx, cancel := context.WithTimeout(ctx, 10*time.Second)
+	defer cancel()
+	<-ctx.Done()
 }
 
 func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.WaitGroup) {
@@ -53,8 +55,13 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 	case <-ctx.Done():
 		return
 	}
-	_, unboundCancel := context.WithCancel(ctx)
-	for {
+	defer l.logger.Warn("loop exited")
+
+	var unboundCtx context.Context
+	var unboundCancel context.CancelFunc = func() {}
+	var waitError chan error
+	triggeredRestart := false
+	for ctx.Err() == nil {
 		if !l.settings.Enabled {
 			// wait for another restart signal to recheck if it is enabled
 			select {
@@ -64,33 +71,34 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 				return
 			}
 		}
-		if ctx.Err() == context.Canceled {
-			unboundCancel()
-			return
-		}
 
 		// Setup
 		if err := l.conf.DownloadRootHints(l.uid, l.gid); err != nil {
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		if err := l.conf.DownloadRootKey(l.uid, l.gid); err != nil {
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		if err := l.conf.MakeUnboundConf(l.settings, l.uid, l.gid); err != nil {
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 
-		// Start command
-		unboundCancel()
-		unboundCtx, unboundCancel := context.WithCancel(ctx)
+		if triggeredRestart {
+			triggeredRestart = false
+			unboundCancel()
+			<-waitError
+			close(waitError)
+		}
+		unboundCtx, unboundCancel = context.WithCancel(context.Background())
 		stream, waitFn, err := l.conf.Start(unboundCtx, l.settings.VerbosityDetailsLevel)
 		if err != nil {
 			unboundCancel()
 			l.fallbackToUnencryptedDNS()
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
+			continue
 		}
 
 		// Started successfully
@@ -98,16 +106,15 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 			command.MergeName("unbound"), command.MergeColor(constants.ColorUnbound()))
 		l.conf.UseDNSInternally(net.IP{127, 0, 0, 1})                         // use Unbound
 		if err := l.conf.UseDNSSystemWide(net.IP{127, 0, 0, 1}); err != nil { // use Unbound
-			unboundCancel()
-			l.fallbackToUnencryptedDNS()
-			l.attemptingRestart(err)
+			l.logger.Error(err)
 		}
 		if err := l.conf.WaitForUnbound(); err != nil {
 			unboundCancel()
 			l.fallbackToUnencryptedDNS()
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
+			continue
 		}
-		waitError := make(chan error)
+		waitError = make(chan error)
 		go func() {
 			err := waitFn() // blocking
 			waitError <- err
@@ -122,16 +129,17 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 			close(waitError)
 			return
 		case <-restart: // triggered restart
-			unboundCancel()
-			close(waitError)
 			l.logger.Info("restarting")
+			// unboundCancel occurs next loop run when the setup is complete
+			triggeredRestart = true
 		case err := <-waitError: // unexpected error
-			unboundCancel()
 			close(waitError)
+			unboundCancel()
 			l.fallbackToUnencryptedDNS()
-			l.attemptingRestart(err)
+			l.logAndWait(ctx, err)
 		}
 	}
+	unboundCancel()
 }
 
 func (l *looper) fallbackToUnencryptedDNS() {
diff --git a/internal/publicip/loop.go b/internal/publicip/loop.go
index cecb1031..be374288 100644
--- a/internal/publicip/loop.go
+++ b/internal/publicip/loop.go
@@ -36,10 +36,12 @@ func NewLooper(client network.Client, logger logging.Logger, fileManager files.F
 	}
 }
 
-func (l *looper) logAndWait(err error) {
+func (l *looper) logAndWait(ctx context.Context, err error) {
 	l.logger.Error(err)
 	l.logger.Info("retrying in 5 seconds")
-	time.Sleep(5 * time.Second)
+	ctx, cancel := context.WithTimeout(ctx, 5*time.Second)
+	defer cancel() // just for the linter
+	<-ctx.Done()
 }
 
 func (l *looper) Run(ctx context.Context, restart <-chan struct{}) {
@@ -48,10 +50,12 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}) {
 	case <-ctx.Done():
 		return
 	}
-	for {
+	defer l.logger.Warn("loop exited")
+
+	for ctx.Err() == nil {
 		ip, err := l.getter.Get()
 		if err != nil {
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		l.logger.Info("Public IP address is %s", ip)
@@ -61,7 +65,7 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}) {
 			files.Ownership(l.uid, l.gid),
 			files.Permissions(0600))
 		if err != nil {
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		select {
diff --git a/internal/server/server.go b/internal/server/server.go
index 77e34acd..397c9cc0 100644
--- a/internal/server/server.go
+++ b/internal/server/server.go
@@ -37,6 +37,7 @@ func (s *server) Run(ctx context.Context, wg *sync.WaitGroup) {
 		defer wg.Done()
 		<-ctx.Done()
 		s.logger.Warn("context canceled: exiting loop")
+		defer s.logger.Warn("loop exited")
 		shutdownCtx, cancel := context.WithTimeout(context.Background(), 2*time.Second)
 		defer cancel()
 		if err := server.Shutdown(shutdownCtx); err != nil {
diff --git a/internal/shadowsocks/loop.go b/internal/shadowsocks/loop.go
index 05e8fcde..6c398162 100644
--- a/internal/shadowsocks/loop.go
+++ b/internal/shadowsocks/loop.go
@@ -27,10 +27,12 @@ type looper struct {
 	gid          int
 }
 
-func (l *looper) logAndWait(err error) {
+func (l *looper) logAndWait(ctx context.Context, err error) {
 	l.logger.Error(err)
 	l.logger.Info("retrying in 1 minute")
-	time.Sleep(time.Minute)
+	ctx, cancel := context.WithTimeout(ctx, time.Minute)
+	defer cancel() // just for the linter
+	<-ctx.Done()
 }
 
 func NewLooper(conf Configurator, firewallConf firewall.Configurator, settings settings.ShadowSocks, dnsSettings settings.DNS,
@@ -55,7 +57,9 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 	case <-ctx.Done():
 		return
 	}
-	for {
+	defer l.logger.Warn("loop exited")
+
+	for ctx.Err() == nil {
 		nameserver := l.dnsSettings.PlaintextAddress.String()
 		if l.dnsSettings.Enabled {
 			nameserver = "127.0.0.1"
@@ -68,7 +72,7 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 			l.uid,
 			l.gid)
 		if err != nil {
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		err = l.firewallConf.AllowAnyIncomingOnPort(ctx, l.settings.Port)
@@ -76,11 +80,11 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 		if err != nil {
 			l.logger.Error(err)
 		}
-		shadowsocksCtx, shadowsocksCancel := context.WithCancel(ctx)
-		stdout, stderr, waitFn, err := l.conf.Start(ctx, "0.0.0.0", l.settings.Port, l.settings.Password, l.settings.Log)
+		shadowsocksCtx, shadowsocksCancel := context.WithCancel(context.Background())
+		stdout, stderr, waitFn, err := l.conf.Start(shadowsocksCtx, "0.0.0.0", l.settings.Port, l.settings.Password, l.settings.Log)
 		if err != nil {
 			shadowsocksCancel()
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		go l.streamMerger.Merge(shadowsocksCtx, stdout,
@@ -102,13 +106,12 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 		case <-restart: // triggered restart
 			l.logger.Info("restarting")
 			shadowsocksCancel()
+			<-waitError
 			close(waitError)
 		case err := <-waitError: // unexpected error
-			l.logger.Warn(err)
-			l.logger.Info("restarting")
 			shadowsocksCancel()
 			close(waitError)
-			time.Sleep(time.Second)
+			l.logAndWait(ctx, err)
 		}
 	}
 }
diff --git a/internal/tinyproxy/loop.go b/internal/tinyproxy/loop.go
index b44e37ec..fbd9580f 100644
--- a/internal/tinyproxy/loop.go
+++ b/internal/tinyproxy/loop.go
@@ -26,10 +26,12 @@ type looper struct {
 	gid          int
 }
 
-func (l *looper) logAndWait(err error) {
+func (l *looper) logAndWait(ctx context.Context, err error) {
 	l.logger.Error(err)
 	l.logger.Info("retrying in 1 minute")
-	time.Sleep(time.Minute)
+	ctx, cancel := context.WithTimeout(ctx, time.Minute)
+	defer cancel() // just for the linter
+	<-ctx.Done()
 }
 
 func NewLooper(conf Configurator, firewallConf firewall.Configurator, settings settings.TinyProxy,
@@ -53,7 +55,9 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 	case <-ctx.Done():
 		return
 	}
-	for {
+	defer l.logger.Warn("loop exited")
+
+	for ctx.Err() == nil {
 		err := l.conf.MakeConf(
 			l.settings.LogLevel,
 			l.settings.Port,
@@ -62,7 +66,7 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 			l.uid,
 			l.gid)
 		if err != nil {
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		err = l.firewallConf.AllowAnyIncomingOnPort(ctx, l.settings.Port)
@@ -70,11 +74,11 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 		if err != nil {
 			l.logger.Error(err)
 		}
-		tinyproxyCtx, tinyproxyCancel := context.WithCancel(ctx)
+		tinyproxyCtx, tinyproxyCancel := context.WithCancel(context.Background())
 		stream, waitFn, err := l.conf.Start(tinyproxyCtx)
 		if err != nil {
 			tinyproxyCancel()
-			l.logAndWait(err)
+			l.logAndWait(ctx, err)
 			continue
 		}
 		go l.streamMerger.Merge(tinyproxyCtx, stream,
@@ -94,13 +98,12 @@ func (l *looper) Run(ctx context.Context, restart <-chan struct{}, wg *sync.Wait
 		case <-restart: // triggered restart
 			l.logger.Info("restarting")
 			tinyproxyCancel()
+			<-waitError
 			close(waitError)
 		case err := <-waitError: // unexpected error
-			l.logger.Warn(err)
-			l.logger.Info("restarting")
 			tinyproxyCancel()
 			close(waitError)
-			time.Sleep(time.Second)
+			l.logAndWait(ctx, err)
 		}
 	}
 }