diff --git a/cmd/tk/create_helmrelease.go b/cmd/tk/create_helmrelease.go
index 8b96cd3a..9eebebd9 100644
--- a/cmd/tk/create_helmrelease.go
+++ b/cmd/tk/create_helmrelease.go
@@ -154,7 +154,7 @@ func createHelmReleaseCmdRun(cmd *cobra.Command, args []string) error {
 			return fmt.Errorf("converting values to JSON from %s failed: %w", hrValuesFile, err)
 		}
 
-		helmRelease.Spec.Values = apiextensionsv1.JSON{Raw: json}
+		helmRelease.Spec.Values = &apiextensionsv1.JSON{Raw: json}
 	}
 
 	if export {
diff --git a/cmd/tk/reconcile_helmrelease.go b/cmd/tk/reconcile_helmrelease.go
index 6ac4769b..fa4a4073 100644
--- a/cmd/tk/reconcile_helmrelease.go
+++ b/cmd/tk/reconcile_helmrelease.go
@@ -138,7 +138,7 @@ func isHelmReleaseReady(ctx context.Context, kubeClient client.Client, name, nam
 			if condition.Type == helmv2.ReadyCondition {
 				if condition.Status == corev1.ConditionTrue {
 					return true, nil
-				} else if condition.Status == corev1.ConditionFalse {
+				} else if condition.Status == corev1.ConditionFalse && helmRelease.Status.LastAttemptedRevision != "" {
 					return false, fmt.Errorf(condition.Message)
 				}
 			}