diff --git a/pkg/koyeb/utils.go b/pkg/koyeb/utils.go
index d3540c78..89e07e13 100644
--- a/pkg/koyeb/utils.go
+++ b/pkg/koyeb/utils.go
@@ -74,27 +74,32 @@ func loadYaml(file string) (string, error) {
 }
 
 func watchDeployment(h *ServiceHandler, deploymentId string) {
-	numAttemptsOnUnhealthy := 12
-	retryCount := 0
-	retryInterval := 5
+	now := time.Now()
+	prevStatus := koyeb.DEPLOYMENTSTATUS_PENDING
+	retryInterval := 5 * time.Second
+	timeoutAt := time.Minute * 10
 
-	for {
+	for time.Since(now) < timeoutAt {
 		res, resp, err := h.client.DeploymentsApi.GetDeployment(h.ctx, deploymentId).Execute()
 		if err != nil {
 			fatalApiError(err, resp)
 		}
 		currentStatus := res.Deployment.GetStatus()
 
-		log.Infof("Service deployment in progress. Deployment status is %s. Next update in %d seconds.", currentStatus, retryInterval)
+		log.Infof("Service deployment in progress. Deployment status is %q. Next update in %s.", currentStatus, retryInterval)
 
-		if currentStatus == koyeb.DEPLOYMENTSTATUS_ERROR || currentStatus == koyeb.DEPLOYMENTSTATUS_HEALTHY || retryCount >= numAttemptsOnUnhealthy {
-			break
-		} else if currentStatus == koyeb.DEPLOYMENTSTATUS_UNHEALTHY {
-			retryCount += 1
-			retryInterval = 10
-			time.Sleep(time.Duration(retryInterval) * time.Second)
-		} else {
-			time.Sleep(time.Duration(retryInterval) * time.Second)
+		if currentStatus == koyeb.DEPLOYMENTSTATUS_ERROR || currentStatus == koyeb.DEPLOYMENTSTATUS_HEALTHY {
+			if currentStatus == koyeb.DEPLOYMENTSTATUS_ERROR {
+				log.Infof("Service deployment failed. Please check the logs.")
+			}
+			return
+		} else if currentStatus == koyeb.DEPLOYMENTSTATUS_UNHEALTHY && prevStatus != koyeb.DEPLOYMENTSTATUS_UNHEALTHY {
+			timeoutAt = time.Minute * 5
+			now = time.Now()
 		}
+		time.Sleep(retryInterval)
+		prevStatus = currentStatus
 	}
+
+	log.Infof("Service deployment didn't pass health checks. Last status was %q", prevStatus)
 }