diff --git a/test/e2e/upgrade.go b/test/e2e/upgrade.go
index 52ac59d9ef394..cc184b3e1e0c4 100644
--- a/test/e2e/upgrade.go
+++ b/test/e2e/upgrade.go
@@ -60,6 +60,18 @@ func runSimpleUpgradeFlowWorkerNodeVersionForBareMetal(test *framework.ClusterE2
 	test.ValidateHardwareDecommissioned()
 }
 
+func runInPlaceMultipleUpgradesFlow(test *framework.ClusterE2ETest, clusterOpts, clusterOpts2, clusterOpts3 []framework.ClusterE2ETestOpt) {
+	test.CreateCluster()
+	test.UpgradeClusterWithNewConfig(clusterOpts)
+	test.ValidateClusterState()
+	test.UpgradeClusterWithNewConfig(clusterOpts2)
+	test.ValidateClusterState()
+	test.UpgradeClusterWithNewConfig(clusterOpts3)
+	test.ValidateClusterState()
+	test.StopIfFailed()
+	test.DeleteCluster()
+}
+
 // runInPlaceUpgradeFlow makes use of the new ValidateClusterState method instead of ValidateCluster, but we should incorporate this
 // in runSimpleUpgradeFlow itself.
 func runInPlaceUpgradeFlow(test *framework.ClusterE2ETest, clusterOpts ...framework.ClusterE2ETestOpt) {
diff --git a/test/e2e/vsphere_test.go b/test/e2e/vsphere_test.go
index 162672ebbbea5..dfcf5b5451dd9 100644
--- a/test/e2e/vsphere_test.go
+++ b/test/e2e/vsphere_test.go
@@ -3599,6 +3599,58 @@ func TestVSphereKubernetes128UbuntuTo129InPlaceUpgrade_3CP_3Worker(t *testing.T)
 	)
 }
 
+func TestVSphereKubernetes125UbuntuTo128InPlaceUpgrade(t *testing.T) {
+	var kube126clusterOpts []framework.ClusterE2ETestOpt
+	var kube127clusterOpts []framework.ClusterE2ETestOpt
+	var kube128clusterOpts []framework.ClusterE2ETestOpt
+	provider := framework.NewVSphere(t, framework.WithUbuntu125())
+	test := framework.NewClusterE2ETest(
+		t,
+		provider,
+		framework.WithEnvVar(features.VSphereInPlaceEnvVar, "true"),
+	).WithClusterConfig(
+		api.ClusterToConfigFiller(
+			api.WithKubernetesVersion(v1alpha1.Kube125),
+			api.WithStackedEtcdTopology(),
+			api.WithInPlaceUpgradeStrategy(),
+		),
+		api.VSphereToConfigFiller(
+			api.RemoveEtcdVsphereMachineConfig(),
+		),
+		provider.WithKubeVersionAndOS(v1alpha1.Kube125, framework.Ubuntu2004, nil),
+	)
+	kube126clusterOpts = append(
+		kube126clusterOpts,
+		framework.WithClusterUpgrade(
+			api.WithKubernetesVersion(v1alpha1.Kube126),
+			api.WithInPlaceUpgradeStrategy(),
+		),
+		provider.WithProviderUpgrade(provider.Ubuntu126Template()),
+	)
+	kube127clusterOpts = append(
+		kube127clusterOpts,
+		framework.WithClusterUpgrade(
+			api.WithKubernetesVersion(v1alpha1.Kube127),
+			api.WithInPlaceUpgradeStrategy(),
+		),
+		provider.WithProviderUpgrade(provider.Ubuntu127Template()),
+	)
+	kube128clusterOpts = append(
+		kube128clusterOpts,
+		framework.WithClusterUpgrade(
+			api.WithKubernetesVersion(v1alpha1.Kube128),
+			api.WithInPlaceUpgradeStrategy(),
+		),
+		provider.WithProviderUpgrade(provider.Ubuntu128Template()),
+	)
+	runInPlaceMultipleUpgradesFlow(
+		test,
+		kube126clusterOpts,
+		kube127clusterOpts,
+		kube128clusterOpts,
+	)
+}
+
 func TestVSphereKubernetes128UbuntuInPlaceCPScaleUp1To3(t *testing.T) {
 	provider := framework.NewVSphere(t, framework.WithUbuntu128())
 	test := framework.NewClusterE2ETest(