diff --git a/cmd/cli/cli.go b/cmd/cli/cli.go
index 07abf3c..9d01206 100644
--- a/cmd/cli/cli.go
+++ b/cmd/cli/cli.go
@@ -1478,6 +1478,12 @@ func removeOrgFlagsFromArgs(sc *service.Config) {
 
 // newSocketControlClient returns new control client after control server was started.
 func newSocketControlClient(ctx context.Context, s service.Service, dir string) *controlClient {
+	return newSocketControlClientWithTimeout(ctx, s, dir, dialSocketControlServerTimeout)
+}
+
+// newSocketControlClientWithTimeout returns new control client after control server was started.
+// The timeoutDuration controls how long to wait for the server.
+func newSocketControlClientWithTimeout(ctx context.Context, s service.Service, dir string, timeoutDuration time.Duration) *controlClient {
 	// Return early if service is not running.
 	if status, err := s.Status(); err != nil || status != service.StatusRunning {
 		return nil
@@ -1486,7 +1492,7 @@ func newSocketControlClient(ctx context.Context, s service.Service, dir string)
 	bo.LogLongerThan = 10 * time.Second
 
 	cc := newControlClient(filepath.Join(dir, ctrldControlUnixSock))
-	timeout := time.NewTimer(30 * time.Second)
+	timeout := time.NewTimer(timeoutDuration)
 	defer timeout.Stop()
 
 	// The socket control server may not start yet, so attempt to ping
@@ -1807,7 +1813,7 @@ func resetDnsTask(p *prog, s service.Service, isCtrldInstalled bool, ir *ifaceRe
 }
 
 // doValidateCdRemoteConfig fetches and validates custom config for cdUID.
-func doValidateCdRemoteConfig(cdUID string, fatal bool) {
+func doValidateCdRemoteConfig(cdUID string, fatal bool) error {
 	rc, err := controld.FetchResolverConfig(cdUID, rootCmd.Version, cdDev)
 	if err != nil {
 		logger := mainLog.Load().Fatal()
@@ -1816,7 +1822,7 @@ func doValidateCdRemoteConfig(cdUID string, fatal bool) {
 		}
 		logger.Err(err).Err(err).Msgf("failed to fetch resolver uid: %s", cdUID)
 		if !fatal {
-			return
+			return err
 		}
 	}
 	// validateCdRemoteConfig clobbers v, saving it here to restore later.
@@ -1847,6 +1853,7 @@ func doValidateCdRemoteConfig(cdUID string, fatal bool) {
 		mainLog.Load().Warn().Msg("disregarding invalid custom config")
 	}
 	v = oldV
+	return nil
 }
 
 // uninstallInvalidCdUID performs self-uninstallation because the ControlD device does not exist.
diff --git a/cmd/cli/commands.go b/cmd/cli/commands.go
index d340574..49dfb8f 100644
--- a/cmd/cli/commands.go
+++ b/cmd/cli/commands.go
@@ -30,6 +30,9 @@ import (
 	"github.com/Control-D-Inc/ctrld/internal/router"
 )
 
+// dialSocketControlServerTimeout is the default timeout to wait when ping control server.
+const dialSocketControlServerTimeout = 30 * time.Second
+
 func initLogCmd() *cobra.Command {
 	warnRuntimeLoggingNotEnabled := func() {
 		mainLog.Load().Warn().Msg("runtime debug logging is not enabled")
@@ -373,7 +376,7 @@ NOTE: running "ctrld start" without any arguments will start already installed c
 			}
 
 			if cdUID != "" {
-				doValidateCdRemoteConfig(cdUID, true)
+				_ = doValidateCdRemoteConfig(cdUID, true)
 			} else if uid := cdUIDFromProvToken(); uid != "" {
 				cdUID = uid
 				mainLog.Load().Debug().Msg("using uid from provision token")
@@ -697,8 +700,9 @@ func initRestartCmd() *cobra.Command {
 
 			initInteractiveLogging()
 
+			var validateConfigErr error
 			if cdMode {
-				doValidateCdRemoteConfig(cdUID, false)
+				validateConfigErr = doValidateCdRemoteConfig(cdUID, false)
 			}
 
 			if ir := runningIface(s); ir != nil {
@@ -752,12 +756,18 @@ func initRestartCmd() *cobra.Command {
 
 			if doRestart() {
 				if dir, err := socketDir(); err == nil {
-					cc := newSocketControlClient(context.TODO(), s, dir)
-					if cc == nil {
-						mainLog.Load().Error().Msg("Could not complete service restart")
-						os.Exit(1)
+					timeout := dialSocketControlServerTimeout
+					// If we failed to validate remote config above, it's likely that
+					// we are having problem with network connection. So using a shorter
+					// timeout than default one for better UX.
+					if validateConfigErr != nil {
+						timeout = 5 * time.Second
+					}
+					if cc := newSocketControlClientWithTimeout(context.TODO(), s, dir, timeout); cc != nil {
+						_, _ = cc.post(ifacePath, nil)
+					} else {
+						mainLog.Load().Warn().Err(err).Msg("Service was restarted, but ctrld process may not be ready yet")
 					}
-					_, _ = cc.post(ifacePath, nil)
 				} else {
 					mainLog.Load().Warn().Err(err).Msg("Service was restarted, but could not ping the control server")
 				}