diff --git a/cli/cmd/cluster_prepare.go b/cli/cmd/cluster_prepare.go
index 7b195300..f657fa94 100644
--- a/cli/cmd/cluster_prepare.go
+++ b/cli/cmd/cluster_prepare.go
@@ -181,10 +181,6 @@ func (r *runners) prepareCluster(_ *cobra.Command, args []string) error {
 		return errors.Wrap(err, "get cluster kubeconfig")
 	}
 
-	if len(release.Charts) == 0 {
-		return errors.New("no charts found in release")
-	}
-
 	isReleaseReady, err := isReleaseReady(r, log, *release)
 	if err != nil || !isReleaseReady {
 		return errors.Wrap(err, "release not ready")
@@ -372,45 +368,54 @@ func prepareRelease(r *runners, log *logger.Logger) (*types.ReleaseInfo, error)
 }
 
 func isReleaseReady(r *runners, log *logger.Logger, release types.ReleaseInfo) (bool, error) {
-	isReleaseReady := false
-	for !isReleaseReady {
-		appRelease, err := r.api.GetRelease(r.appID, r.appType, release.Sequence)
-		if err != nil {
-			return false, errors.Wrap(err, "failed to get release")
-		}
+	if len(release.Charts) == 0 {
+		return false, errors.New("no charts found in release")
+	}
 
-		if len(appRelease.Charts) == 0 {
-			return false, errors.New("no charts found in release")
-		}
+	timeout := time.Duration(10*len(release.Charts)) * time.Second
+	timer := time.NewTimer(timeout)
+	defer timer.Stop()
+
+	for {
+		select {
+		case <-timer.C:
+			return false, errors.Errorf("timed out waiting for release to be ready after %s", timeout)
+		default:
+			appRelease, err := r.api.GetRelease(r.appID, r.appType, release.Sequence)
+			if err != nil {
+				return false, errors.Wrap(err, "failed to get release")
+			}
+
+			ready, err := areReleaseChartsPushed(appRelease.Charts)
+			if err != nil {
+				return false, errors.Wrap(err, "failed to check release charts")
+			} else if ready {
+				return true, nil
+			}
 
-		releaseChartsReady, err := areReleaseChartsReady(appRelease.Charts)
-		if err != nil {
-			return false, errors.Wrap(err, "failed to get release")
-		}
-		if !releaseChartsReady {
 			time.Sleep(time.Second * 2)
-			continue
 		}
-
-		isReleaseReady = true
 	}
-
-	return true, nil
 }
 
-func areReleaseChartsReady(charts []types.Chart) (bool, error) {
-	areChartsPushed := false
+func areReleaseChartsPushed(charts []types.Chart) (bool, error) {
+	if len(charts) == 0 {
+		return false, errors.New("no charts found in release")
+	}
+
+	pushedChartsCount := 0
 	for _, chart := range charts {
-		if chart.Status == types.ChartStatusPushing || chart.Status == types.ChartStatusUnknown {
-			areChartsPushed = false
-			continue
-		} else if chart.Status == types.ChartStatusPushed {
-			areChartsPushed = true
-		} else if chart.Status == types.ChartStatusError {
+		switch chart.Status {
+		case types.ChartStatusPushed:
+			pushedChartsCount++
+		case types.ChartStatusUnknown, types.ChartStatusPushing:
+			// wait for the chart to be pushed
+		case types.ChartStatusError:
 			return false, errors.Errorf("chart %q failed to push: %s", chart.Name, chart.Error)
-		} else {
+		default:
 			return false, errors.Errorf("unknown release chart status %q", chart.Status)
 		}
 	}
-	return areChartsPushed, nil
+
+	return pushedChartsCount == len(charts), nil
 }
diff --git a/cli/cmd/cluster_prepare_test.go b/cli/cmd/cluster_prepare_test.go
index f88f1812..7ef582b8 100644
--- a/cli/cmd/cluster_prepare_test.go
+++ b/cli/cmd/cluster_prepare_test.go
@@ -13,8 +13,8 @@ func Test_areReleaseChartsReady(t *testing.T) {
 		want    bool
 		wantErr bool
 	}{
-		{"nil charts", nil, false, false},
-		{"no charts", []types.Chart{}, false, false},
+		{"nil charts", nil, false, true},
+		{"no charts", []types.Chart{}, false, true},
 		{"one chart, no status", []types.Chart{{}}, false, true},
 		{"one chart, status unkown", []types.Chart{{Status: types.ChartStatusUnknown}}, false, false},
 		{"one chart, status pushing", []types.Chart{{Status: types.ChartStatusPushing}}, false, false},
@@ -35,7 +35,7 @@ func Test_areReleaseChartsReady(t *testing.T) {
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			got, err := areReleaseChartsReady(tt.charts)
+			got, err := areReleaseChartsPushed(tt.charts)
 			if (err != nil) != tt.wantErr {
 				t.Errorf("areReleaseChartsReady() error = %v, wantErr %v", err, tt.wantErr)
 				return