diff --git a/pkg/volume/util/nested_volumes.go b/pkg/volume/util/nested_volumes.go
index 2ceab422382..27a6c29cd98 100644
--- a/pkg/volume/util/nested_volumes.go
+++ b/pkg/volume/util/nested_volumes.go
@@ -51,8 +51,14 @@ func getNestedMountpoints(name, baseDir string, pod v1.Pod) ([]string, error) {
 				return fmt.Errorf("invalid container mount point %v", myMountPoint)
 			}
 			myMPSlash := myMountPoint + string(os.PathSeparator)
-			// The previously found nested mountpoint (or "" if none found yet)
-			prevNestedMP := ""
+			// The previously found nested mountpoints.
+			// NOTE: We can't simply rely on sort.Strings to have all the mountpoints sorted and
+			// grouped. For example, the following strings are sorted in this exact order:
+			// /dir/nested, /dir/nested-vol, /dir/nested.vol, /dir/nested/double, /dir/nested2
+			// The issue is a bit worse for Windows paths, since the \'s value is higher than /'s:
+			// \dir\nested, \dir\nested-vol, \dir\nested.vol, \dir\nested2, \dir\nested\double
+			// Because of this, we should use a list of previously mounted mountpoints, rather than only one.
+			prevNestedMPs := []string{}
 			// examine each mount point to see if it's nested beneath this volume
 			// (but skip any that are double-nested beneath this volume)
 			// For example, if this volume is mounted as /dir and other volumes are mounted
@@ -61,11 +67,19 @@ func getNestedMountpoints(name, baseDir string, pod v1.Pod) ([]string, error) {
 				if !strings.HasPrefix(mp, myMPSlash) {
 					continue // skip -- not nested beneath myMountPoint
 				}
-				if prevNestedMP != "" && strings.HasPrefix(mp, prevNestedMP) {
+
+				isNested := false
+				for _, prevNestedMP := range prevNestedMPs {
+					if strings.HasPrefix(mp, prevNestedMP) {
+						isNested = true
+						break
+					}
+				}
+				if isNested {
 					continue // skip -- double nested beneath myMountPoint
 				}
 				// since this mount point is nested, remember it so that we can check that following ones aren't nested beneath this one
-				prevNestedMP = mp + string(os.PathSeparator)
+				prevNestedMPs = append(prevNestedMPs, mp+string(os.PathSeparator))
 				retval = append(retval, mp[len(myMPSlash):])
 			}
 		}
diff --git a/pkg/volume/util/nested_volumes_test.go b/pkg/volume/util/nested_volumes_test.go
index f4f4adda0b8..b136eaeaf75 100644
--- a/pkg/volume/util/nested_volumes_test.go
+++ b/pkg/volume/util/nested_volumes_test.go
@@ -89,7 +89,7 @@ func TestGetNestedMountpoints(t *testing.T) {
 		{
 			name:     "Unsorted Nested Pod",
 			err:      false,
-			expected: sets.NewString("nested", "nested2"),
+			expected: sets.NewString("nested", "nested2", "nested-vol", "nested.vol"),
 			volname:  "vol1",
 			pod: v1.Pod{
 				ObjectMeta: metav1.ObjectMeta{
@@ -105,6 +105,9 @@ func TestGetNestedMountpoints(t *testing.T) {
 								{MountPath: "/dir/nested", Name: "vol2"},
 								{MountPath: "/ignore2", Name: "vol5"},
 								{MountPath: "/dir", Name: "vol1"},
+								{MountPath: "/dir/nested-vol", Name: "vol6"},
+								{MountPath: "/dir/nested.vol", Name: "vol7"},
+								{MountPath: "/dir/nested2/double", Name: "vol8"},
 								{MountPath: "/dir/nested2", Name: "vol3"},
 							},
 						},