diff --git a/pkg/embeddedcluster/monitor.go b/pkg/embeddedcluster/monitor.go
index 4cb5d9f0ad..3d0e1d0eca 100644
--- a/pkg/embeddedcluster/monitor.go
+++ b/pkg/embeddedcluster/monitor.go
@@ -2,6 +2,7 @@ package embeddedcluster
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"sync"
 	"time"
@@ -18,6 +19,7 @@ var stateMut = sync.Mutex{}
 // it starts the upgrade process. We only start an upgrade if the following conditions are met:
 // - The app has an embedded cluster configuration.
 // - The app embedded cluster configuration differs from the current embedded cluster config.
+// - The current cluster config (as part of the Installation object) already exists in the cluster.
 func MaybeStartClusterUpgrade(ctx context.Context, client kubernetes.Interface, store store.Store, conf *v1beta1.Config) error {
 	if conf == nil {
 		return nil
@@ -33,6 +35,13 @@ func MaybeStartClusterUpgrade(ctx context.Context, client kubernetes.Interface,
 
 	spec := conf.Spec
 	if upgrade, err := RequiresUpgrade(ctx, spec); err != nil {
+		// if there is no installation object we can't start an upgrade. this is a valid
+		// scenario specially during cluster bootstrap. as we do not need to upgrade the
+		// cluster just after its installation we can return nil here.
+		// (the cluster in the first kots version will match the cluster installed during bootstrap)
+		if errors.Is(err, ErrNoInstallations) {
+			return nil
+		}
 		return fmt.Errorf("failed to check if upgrade is required: %w", err)
 	} else if !upgrade {
 		return nil
diff --git a/pkg/embeddedcluster/util.go b/pkg/embeddedcluster/util.go
index ffcaacee0e..6487ee3601 100644
--- a/pkg/embeddedcluster/util.go
+++ b/pkg/embeddedcluster/util.go
@@ -21,6 +21,9 @@ import (
 const configMapName = "embedded-cluster-config"
 const configMapNamespace = "embedded-cluster"
 
+// ErrNoInstallations is returned when no installation object is found in the cluster.
+var ErrNoInstallations = fmt.Errorf("no installations found")
+
 // ReadConfigMap will read the Kurl config from a configmap
 func ReadConfigMap(client kubernetes.Interface) (*corev1.ConfigMap, error) {
 	return client.CoreV1().ConfigMaps(configMapNamespace).Get(context.TODO(), configMapName, metav1.GetOptions{})
@@ -96,7 +99,7 @@ func GetCurrentInstallation(ctx context.Context) (*embeddedclusterv1beta1.Instal
 		return nil, fmt.Errorf("failed to list installations: %w", err)
 	}
 	if len(installationList.Items) == 0 {
-		return nil, fmt.Errorf("no installations found")
+		return nil, ErrNoInstallations
 	}
 	items := installationList.Items
 	sort.SliceStable(items, func(i, j int) bool {