diff --git a/cmd/gluetun/main.go b/cmd/gluetun/main.go
index d81b9b20..d868cea2 100644
--- a/cmd/gluetun/main.go
+++ b/cmd/gluetun/main.go
@@ -253,9 +253,10 @@ func _main(ctx context.Context, buildInfo models.BuildInformation,
 	} // TODO move inside firewall?
 
 	wg := &sync.WaitGroup{}
+	healthy := make(chan bool)
 
 	openvpnLooper := openvpn.NewLooper(allSettings.OpenVPN, nonRootUsername, puid, pgid, allServers,
-		ovpnConf, firewallConf, routingConf, logger, httpClient, os.OpenFile, tunnelReadyCh, cancel)
+		ovpnConf, firewallConf, routingConf, logger, httpClient, os.OpenFile, tunnelReadyCh, healthy, cancel)
 	wg.Add(1)
 	// wait for restartOpenvpn
 	go openvpnLooper.Run(ctx, wg)
@@ -302,7 +303,7 @@ func _main(ctx context.Context, buildInfo models.BuildInformation,
 	healthcheckServer := healthcheck.NewServer(
 		constants.HealthcheckAddress, logger)
 	wg.Add(1)
-	go healthcheckServer.Run(ctx, wg)
+	go healthcheckServer.Run(ctx, healthy, wg)
 
 	// Start openvpn for the first time in a blocking call
 	// until openvpn is launched
diff --git a/internal/healthcheck/health.go b/internal/healthcheck/health.go
index 4cb90bfa..c51d3020 100644
--- a/internal/healthcheck/health.go
+++ b/internal/healthcheck/health.go
@@ -10,7 +10,7 @@ import (
 	"time"
 )
 
-func (s *server) runHealthcheckLoop(ctx context.Context, wg *sync.WaitGroup) {
+func (s *server) runHealthcheckLoop(ctx context.Context, healthy chan<- bool, wg *sync.WaitGroup) {
 	defer wg.Done()
 	for {
 		previousErr := s.handler.getErr()
@@ -18,6 +18,12 @@ func (s *server) runHealthcheckLoop(ctx context.Context, wg *sync.WaitGroup) {
 		err := healthCheck(ctx, s.resolver)
 		s.handler.setErr(err)
 
+		// Notify the healthy channel, or not if it's already full
+		select {
+		case healthy <- err == nil:
+		default:
+		}
+
 		if previousErr != nil && err == nil {
 			s.logger.Info("healthy!")
 		} else if previousErr == nil && err != nil {
@@ -36,8 +42,8 @@ func (s *server) runHealthcheckLoop(ctx context.Context, wg *sync.WaitGroup) {
 			}
 			continue
 		}
-		// Success, check again in 10 minutes
-		const period = 10 * time.Minute
+		// Success, check again in 5 seconds
+		const period = 5 * time.Second
 		timer := time.NewTimer(period)
 		select {
 		case <-ctx.Done():
diff --git a/internal/healthcheck/server.go b/internal/healthcheck/server.go
index d7d42914..69b7c988 100644
--- a/internal/healthcheck/server.go
+++ b/internal/healthcheck/server.go
@@ -12,7 +12,7 @@ import (
 )
 
 type Server interface {
-	Run(ctx context.Context, wg *sync.WaitGroup)
+	Run(ctx context.Context, healthy chan<- bool, wg *sync.WaitGroup)
 }
 
 type server struct {
@@ -32,12 +32,12 @@ func NewServer(address string, logger logging.Logger) Server {
 	}
 }
 
-func (s *server) Run(ctx context.Context, wg *sync.WaitGroup) {
+func (s *server) Run(ctx context.Context, healthy chan<- bool, wg *sync.WaitGroup) {
 	defer wg.Done()
 
 	internalWg := &sync.WaitGroup{}
 	internalWg.Add(1)
-	go s.runHealthcheckLoop(ctx, internalWg)
+	go s.runHealthcheckLoop(ctx, healthy, internalWg)
 
 	server := http.Server{
 		Addr:    s.address,
diff --git a/internal/openvpn/loop.go b/internal/openvpn/loop.go
index 750a5be3..7788561d 100644
--- a/internal/openvpn/loop.go
+++ b/internal/openvpn/loop.go
@@ -45,6 +45,7 @@ type looper struct {
 	client           *http.Client
 	openFile         os.OpenFileFunc
 	tunnelReady      chan<- struct{}
+	healthy          <-chan bool
 	cancel           context.CancelFunc
 	// Internal channels and locks
 	loopLock           sync.Mutex
@@ -54,15 +55,19 @@ type looper struct {
 	portForwardSignals chan net.IP
 	crashed            bool
 	backoffTime        time.Duration
+	healthWaitTime     time.Duration
 }
 
-const defaultBackoffTime = 15 * time.Second
+const (
+	defaultBackoffTime    = 15 * time.Second
+	defaultHealthWaitTime = 6 * time.Second
+)
 
 func NewLooper(settings configuration.OpenVPN,
 	username string, puid, pgid int, allServers models.AllServers,
 	conf Configurator, fw firewall.Configurator, routing routing.Routing,
 	logger logging.Logger, client *http.Client, openFile os.OpenFileFunc,
-	tunnelReady chan<- struct{}, cancel context.CancelFunc) Looper {
+	tunnelReady chan<- struct{}, healthy <-chan bool, cancel context.CancelFunc) Looper {
 	return &looper{
 		state: state{
 			status:     constants.Stopped,
@@ -80,6 +85,7 @@ func NewLooper(settings configuration.OpenVPN,
 		client:             client,
 		openFile:           openFile,
 		tunnelReady:        tunnelReady,
+		healthy:            healthy,
 		cancel:             cancel,
 		start:              make(chan struct{}),
 		running:            make(chan models.LoopStatus),
@@ -87,6 +93,7 @@ func NewLooper(settings configuration.OpenVPN,
 		stopped:            make(chan struct{}),
 		portForwardSignals: make(chan net.IP),
 		backoffTime:        defaultBackoffTime,
+		healthWaitTime:     defaultHealthWaitTime,
 	}
 }
 
@@ -215,6 +222,22 @@ func (l *looper) Run(ctx context.Context, wg *sync.WaitGroup) { //nolint:gocogni
 				l.logAndWait(ctx, err)
 				l.crashed = true
 				stayHere = false
+			case healthy := <-l.healthy:
+				if healthy {
+					continue
+				}
+				// ensure it stays unhealthy for some time before restarting it
+				healthy = l.waitForHealth(ctx)
+				if healthy || ctx.Err() != nil {
+					continue
+				}
+				l.crashed = true // flag as crashed
+				l.state.setStatusWithLock(constants.Stopping)
+				l.logger.Warn("unhealthy program: restarting openvpn")
+				openvpnCancel()
+				<-waitError
+				l.state.setStatusWithLock(constants.Stopped)
+				stayHere = false
 			}
 		}
 		close(waitError)
@@ -240,6 +263,35 @@ func (l *looper) logAndWait(ctx context.Context, err error) {
 	}
 }
 
+// waitForHealth waits for a true healthy signal
+// after restarting openvpn in order to avoid restarting
+// openvpn in a loop as it requires a few seconds to connect.
+func (l *looper) waitForHealth(ctx context.Context) (healthy bool) {
+	l.logger.Info("unhealthy program: waiting %s for it to change to healthy", l.healthWaitTime)
+	timer := time.NewTimer(l.healthWaitTime)
+	l.healthWaitTime *= 2
+	for {
+		select {
+		case healthy = <-l.healthy:
+			if !healthy {
+				break
+			}
+			if !timer.Stop() {
+				<-timer.C
+			}
+			l.healthWaitTime = defaultHealthWaitTime
+			return true
+		case <-timer.C:
+			return false
+		case <-ctx.Done():
+			if !timer.Stop() {
+				<-timer.C
+			}
+			return false
+		}
+	}
+}
+
 // portForward is a blocking operation which may or may not be infinite.
 // You should therefore always call it in a goroutine.
 func (l *looper) portForward(ctx context.Context, wg *sync.WaitGroup,