diff --git a/pkg/cluster/storage.go b/pkg/cluster/storage.go
index 40858aa2301..4a5e407c710 100644
--- a/pkg/cluster/storage.go
+++ b/pkg/cluster/storage.go
@@ -186,6 +186,13 @@ func (c *Cluster) storageBootstrap(ctx context.Context) error {
 			// that's AFTER generating CA certs and tokens. If the config is updated to set the
 			// matching key, further startups will still be blocked pending cleanup of the
 			// "newer" files as per the bootstrap reconciliation code.
+
+			_, err = getBootstrapValues(ctx, storageClient)
+			if err != nil {
+				return err
+			}
+			logrus.Info("Datastore connection validated successfully, proceeding with bootstrap data generation")
+
 			c.saveBootstrap = true
 			return nil
 		}
@@ -269,6 +276,30 @@ func (c *Cluster) getBootstrapData(ctx context.Context, token string) ([]byte, e
 	return decrypt(token, value.Data)
 }
 
+// getBootstrapValues returns the value of all keys under the "/bootstrap" prefix, with a 10 second timeout. 
+func getBootstrapValues(ctx context.Context, storageClient client.Client) ([]client.Value, error) {
+	var bootstrapList []client.Value
+	var err error
+
+	if err := wait.PollUntilContextCancel(ctx, 5*time.Second, true, func(ctx context.Context) (bool, error) {
+		operationCtx, operationCancel := context.WithTimeout(ctx, 10*time.Second)
+		defer operationCancel()
+	
+		bootstrapList, err = storageClient.List(operationCtx, "/bootstrap", 0)
+		if err != nil {
+			if errors.Is(err, rpctypes.ErrGPRCNotSupportedForLearner) {
+				return false, nil
+			}
+			return false, err
+		}
+		return true, nil
+	}); err != nil {
+		logrus.Errorf("Failed to validate datastore connection: %v", err)
+		return nil, err
+	}
+	return bootstrapList, nil
+}
+
 // getBootstrapKeyFromStorage will list all keys that has prefix /bootstrap and will check for key that is
 // hashed with empty string and will check for any key that is hashed by different token than the one
 // passed to it, it will return error if it finds a key that is hashed with different token and will return
@@ -278,19 +309,8 @@ func getBootstrapKeyFromStorage(ctx context.Context, storageClient client.Client
 	emptyStringKey := storageKey("")
 	tokenKey := storageKey(normalizedToken)
 
-	var bootstrapList []client.Value
-	var err error
-
-	if err := wait.PollUntilContextCancel(ctx, 5*time.Second, true, func(ctx context.Context) (bool, error) {
-		bootstrapList, err = storageClient.List(ctx, "/bootstrap", 0)
-		if err != nil {
-			if errors.Is(err, rpctypes.ErrGPRCNotSupportedForLearner) {
-				return false, nil
-			}
-			return false, err
-		}
-		return true, nil
-	}); err != nil {
+	bootstrapList, err := getBootstrapValues(ctx, storageClient)
+	if err != nil {
 		return nil, false, err
 	}