diff --git a/cmd/kubeadm/app/phases/upgrade/BUILD b/cmd/kubeadm/app/phases/upgrade/BUILD
index a34d3e214dd..379c8361e6a 100644
--- a/cmd/kubeadm/app/phases/upgrade/BUILD
+++ b/cmd/kubeadm/app/phases/upgrade/BUILD
@@ -45,6 +45,7 @@ go_library(
         "//staging/src/k8s.io/client-go/kubernetes:go_default_library",
         "//staging/src/k8s.io/client-go/pkg/version:go_default_library",
         "//vendor/github.com/pkg/errors:go_default_library",
+        "//vendor/k8s.io/utils/pointer:go_default_library",
     ],
 )
 
diff --git a/cmd/kubeadm/app/phases/upgrade/prepull.go b/cmd/kubeadm/app/phases/upgrade/prepull.go
index 668e2735005..03c4d0f500e 100644
--- a/cmd/kubeadm/app/phases/upgrade/prepull.go
+++ b/cmd/kubeadm/app/phases/upgrade/prepull.go
@@ -22,13 +22,14 @@ import (
 
 	"github.com/pkg/errors"
 	apps "k8s.io/api/apps/v1"
-	"k8s.io/api/core/v1"
+	v1 "k8s.io/api/core/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	clientset "k8s.io/client-go/kubernetes"
 	kubeadmapi "k8s.io/kubernetes/cmd/kubeadm/app/apis/kubeadm"
 	"k8s.io/kubernetes/cmd/kubeadm/app/constants"
 	"k8s.io/kubernetes/cmd/kubeadm/app/images"
 	"k8s.io/kubernetes/cmd/kubeadm/app/util/apiclient"
+	utilpointer "k8s.io/utils/pointer"
 )
 
 const (
@@ -183,6 +184,11 @@ func buildPrePullDaemonSet(component, image string) *apps.DaemonSet {
 					},
 					Tolerations:                   []v1.Toleration{constants.ControlPlaneToleration},
 					TerminationGracePeriodSeconds: &gracePeriodSecs,
+					// Explicitly add a PodSecurityContext to allow these Pods to run as non-root.
+					// This prevents restrictive PSPs from blocking the Pod creation.
+					SecurityContext: &v1.PodSecurityContext{
+						RunAsUser: utilpointer.Int64Ptr(999),
+					},
 				},
 			},
 		},