diff --git a/bootstrapper/internal/helm/helm.go b/bootstrapper/internal/helm/helm.go
index 1b9027e2a..8061eca94 100644
--- a/bootstrapper/internal/helm/helm.go
+++ b/bootstrapper/internal/helm/helm.go
@@ -15,6 +15,7 @@ import (
 	"net"
 	"os/exec"
 	"strconv"
+	"strings"
 	"time"
 
 	"github.com/edgelesssys/constellation/v2/bootstrapper/internal/kubernetes/k8sapi"
@@ -188,6 +189,11 @@ func (h *Client) installCiliumGCP(ctx context.Context, kubectl k8sapi.Client, re
 // The function will wait 30 seconds before retrying a failed installation attempt.
 // After 5 minutes the retrier will be canceld and the function returns with an error.
 func (h *Client) install(ctx context.Context, chartRaw []byte, values map[string]any) error {
+	retriable := func(err error) bool {
+		return errors.Is(err, wait.ErrWaitTimeout) ||
+			strings.Contains(err.Error(), "connection refused")
+	}
+
 	reader := bytes.NewReader(chartRaw)
 	chart, err := loader.LoadArchive(reader)
 	if err != nil {
@@ -200,7 +206,7 @@ func (h *Client) install(ctx context.Context, chartRaw []byte, values map[string
 		values,
 		h.log,
 	}
-	retrier := retry.NewIntervalRetrier(doer, 30*time.Second, isTimeoutErr)
+	retrier := retry.NewIntervalRetrier(doer, 30*time.Second, retriable)
 
 	// Since we have no precise retry condition we want to stop retrying after 5 minutes.
 	// The helm library only reports a timeout error in the error cases we currently know.
@@ -229,8 +235,3 @@ func (i installDoer) Do(ctx context.Context) error {
 
 	return err
 }
-
-// isTimeoutErr checks if the given error is a timeout error from k8s.io/apimachinery.
-func isTimeoutErr(err error) bool {
-	return errors.Is(err, wait.ErrWaitTimeout)
-}
diff --git a/bootstrapper/internal/kubernetes/kubewaiter/kubewaiter.go b/bootstrapper/internal/kubernetes/kubewaiter/kubewaiter.go
index 8229b1e4a..00e097053 100644
--- a/bootstrapper/internal/kubernetes/kubewaiter/kubewaiter.go
+++ b/bootstrapper/internal/kubernetes/kubewaiter/kubewaiter.go
@@ -9,6 +9,7 @@ package kubewaiter
 
 import (
 	"context"
+	"fmt"
 	"time"
 
 	corev1 "k8s.io/api/core/v1"
@@ -33,7 +34,7 @@ func (w *CloudKubeAPIWaiter) Wait(ctx context.Context, kubernetesClient Kubernet
 	doer := &kubeDoer{kubeClient: kubernetesClient}
 	retrier := retry.NewIntervalRetrier(doer, 5*time.Second, funcAlwaysRetriable)
 	if err := retrier.Do(ctx); err != nil {
-		return doer.Do(context.Background())
+		return fmt.Errorf("waiting for Kubernetes API: %w", err)
 	}
 	return nil
 }