diff --git a/cmd/kubeadm/app/cmd/phases/reset/cleanupnode.go b/cmd/kubeadm/app/cmd/phases/reset/cleanupnode.go
index d78a2926d91..01bbab89f4d 100644
--- a/cmd/kubeadm/app/cmd/phases/reset/cleanupnode.go
+++ b/cmd/kubeadm/app/cmd/phases/reset/cleanupnode.go
@@ -84,11 +84,15 @@ func runCleanupNode(c workflow.RunData) error {
 		// Try to unmount mounted directories under kubeadmconstants.KubeletRunDirectory in order to be able to remove the kubeadmconstants.KubeletRunDirectory directory later
 		fmt.Printf("[reset] Unmounting mounted directories in %q\n", kubeadmconstants.KubeletRunDirectory)
 		// In case KubeletRunDirectory holds a symbolic link, evaluate it
-		kubeletRunDir, err := absoluteKubeletRunDirectory()
-		if err == nil {
-			// Only clean absoluteKubeletRunDirectory if umountDirsCmd passed without error
-			dirsToClean = append(dirsToClean, kubeletRunDir)
+		kubeletRunDirectory, err := absoluteKubeletRunDirectory()
+		if err != nil {
+			return err
 		}
+		// Unmount all mount paths under kubeletRunDirectory
+		if err := unmountKubeletDirectory(kubeletRunDirectory); err != nil {
+			return err
+		}
+		dirsToClean = append(dirsToClean, kubeletRunDirectory)
 	} else {
 		fmt.Printf("[reset] Would unmount mounted directories in %q\n", kubeadmconstants.KubeletRunDirectory)
 	}
@@ -131,13 +135,7 @@ func runCleanupNode(c workflow.RunData) error {
 func absoluteKubeletRunDirectory() (string, error) {
 	absoluteKubeletRunDirectory, err := filepath.EvalSymlinks(kubeadmconstants.KubeletRunDirectory)
 	if err != nil {
-		klog.Warningf("[reset] Failed to evaluate the %q directory. Skipping its unmount and cleanup: %v\n", kubeadmconstants.KubeletRunDirectory, err)
-		return "", err
-	}
-	err = unmountKubeletDirectory(absoluteKubeletRunDirectory)
-	if err != nil {
-		klog.Warningf("[reset] Failed to unmount mounted directories in %s \n", kubeadmconstants.KubeletRunDirectory)
-		return "", err
+		return "", errors.Wrapf(err, "failed to evaluate the %q directory", kubeadmconstants.KubeletRunDirectory)
 	}
 	return absoluteKubeletRunDirectory, nil
 }
diff --git a/cmd/kubeadm/app/cmd/phases/reset/unmount.go b/cmd/kubeadm/app/cmd/phases/reset/unmount.go
index 1796da898b9..c6fbda56d87 100644
--- a/cmd/kubeadm/app/cmd/phases/reset/unmount.go
+++ b/cmd/kubeadm/app/cmd/phases/reset/unmount.go
@@ -24,7 +24,7 @@ import (
 )
 
 // unmountKubeletDirectory is a NOOP on all but linux.
-func unmountKubeletDirectory(absoluteKubeletRunDirectory string) error {
+func unmountKubeletDirectory(kubeletRunDirectory string) error {
 	klog.Warning("Cannot unmount filesystems on current OS, all mounted file systems will need to be manually unmounted")
 	return nil
 }
diff --git a/cmd/kubeadm/app/cmd/phases/reset/unmount_linux.go b/cmd/kubeadm/app/cmd/phases/reset/unmount_linux.go
index 993ab888dad..f7914b91026 100644
--- a/cmd/kubeadm/app/cmd/phases/reset/unmount_linux.go
+++ b/cmd/kubeadm/app/cmd/phases/reset/unmount_linux.go
@@ -24,30 +24,37 @@ import (
 	"strings"
 	"syscall"
 
+	"github.com/pkg/errors"
+
 	"k8s.io/klog/v2"
+
+	utilerrors "k8s.io/apimachinery/pkg/util/errors"
 )
 
 // unmountKubeletDirectory unmounts all paths that contain KubeletRunDirectory
-func unmountKubeletDirectory(absoluteKubeletRunDirectory string) error {
+func unmountKubeletDirectory(kubeletRunDirectory string) error {
 	raw, err := os.ReadFile("/proc/mounts")
 	if err != nil {
 		return err
 	}
 
-	if !strings.HasSuffix(absoluteKubeletRunDirectory, "/") {
+	if !strings.HasSuffix(kubeletRunDirectory, "/") {
 		// trailing "/" is needed to ensure that possibly mounted /var/lib/kubelet is skipped
-		absoluteKubeletRunDirectory += "/"
+		kubeletRunDirectory += "/"
 	}
 
+	var errList []error
 	mounts := strings.Split(string(raw), "\n")
 	for _, mount := range mounts {
 		m := strings.Split(mount, " ")
-		if len(m) < 2 || !strings.HasPrefix(m[1], absoluteKubeletRunDirectory) {
+		if len(m) < 2 || !strings.HasPrefix(m[1], kubeletRunDirectory) {
 			continue
 		}
+		klog.V(5).Infof("[reset] Unmounting %q", m[1])
 		if err := syscall.Unmount(m[1], 0); err != nil {
-			klog.Warningf("[reset] Failed to unmount mounted directory in %s: %s", absoluteKubeletRunDirectory, m[1])
+			errList = append(errList, errors.WithMessagef(err, "failed to unmount %q", m[1]))
 		}
 	}
-	return nil
+	return errors.Wrapf(utilerrors.NewAggregate(errList),
+		"encountered the following errors while unmounting directories in %q", kubeletRunDirectory)
 }