diff --git a/pkg/controller/cluster/cluster.go b/pkg/controller/cluster/cluster.go
index 83f5beb..a523564 100644
--- a/pkg/controller/cluster/cluster.go
+++ b/pkg/controller/cluster/cluster.go
@@ -123,6 +123,11 @@ func (c *ClusterReconciler) Reconcile(ctx context.Context, req reconcile.Request
 
 	// if there was an error during the reconciliation, return
 	if reconcilerErr != nil {
+		if errors.Is(reconcilerErr, bootstrap.ErrServerNotReady) {
+			log.Info("server not ready, requeueing")
+			return reconcile.Result{RequeueAfter: time.Second * 10}, nil
+		}
+
 		return reconcile.Result{}, reconcilerErr
 	}
 
diff --git a/pkg/controller/cluster/server/bootstrap/bootstrap.go b/pkg/controller/cluster/server/bootstrap/bootstrap.go
index 6b1c48a..82fe9d8 100644
--- a/pkg/controller/cluster/server/bootstrap/bootstrap.go
+++ b/pkg/controller/cluster/server/bootstrap/bootstrap.go
@@ -8,6 +8,7 @@ import (
 	"errors"
 	"fmt"
 	"net/http"
+	"syscall"
 	"time"
 
 	"github.com/rancher/k3k/pkg/apis/k3k.io/v1alpha1"
@@ -17,6 +18,8 @@ import (
 	"sigs.k8s.io/controller-runtime/pkg/client"
 )
 
+var ErrServerNotReady = errors.New("server not ready")
+
 type ControlRuntimeBootstrap struct {
 	ServerCA        content `json:"serverCA"`
 	ServerCAKey     content `json:"serverCAKey"`
@@ -68,6 +71,10 @@ func requestBootstrap(token, serverIP string) (*ControlRuntimeBootstrap, error)
 
 	resp, err := client.Do(req)
 	if err != nil {
+		if errors.Is(err, syscall.ECONNREFUSED) {
+			return nil, ErrServerNotReady
+		}
+
 		return nil, err
 	}
 	defer resp.Body.Close()