diff --git a/archive/tar.go b/archive/tar.go
index fca4a38a3..fd6c07206 100644
--- a/archive/tar.go
+++ b/archive/tar.go
@@ -436,6 +436,9 @@ func (cw *changeWriter) HandleChange(k fs.ChangeKind, p string, f os.FileInfo, e
 			AccessTime: cw.whiteoutT,
 			ChangeTime: cw.whiteoutT,
 		}
+		if err := cw.includeParents(hdr); err != nil {
+			return err
+		}
 		if err := cw.tw.WriteHeader(hdr); err != nil {
 			return errors.Wrap(err, "failed to write whiteout header")
 		}
diff --git a/archive/tar_test.go b/archive/tar_test.go
index ae1ce961a..a6cd0db17 100644
--- a/archive/tar_test.go
+++ b/archive/tar_test.go
@@ -874,6 +874,7 @@ func TestDiffTar(t *testing.T) {
 				fileEntry("d3/l1", []byte("link me"), 0644),
 				dirEntry("d4/", 0755),
 				linkEntry("d4/f1", "d3/l1"),
+				dirEntry("d6/", 0755),
 				whiteoutEntry("d6/l1"),
 				whiteoutEntry("d6/l2"),
 			},
@@ -947,6 +948,46 @@ func TestDiffTar(t *testing.T) {
 				fstest.Link("/d3/f1", "/d4/l1"),
 			),
 		},
+		{
+			name: "WhiteoutIncludesParents",
+			validators: []tarEntryValidator{
+				dirEntry("d1/", 0755),
+				whiteoutEntry("d1/f1"),
+				dirEntry("d2/", 0755),
+				whiteoutEntry("d2/f1"),
+				fileEntry("d2/f2", []byte("content"), 0777),
+				dirEntry("d3/", 0755),
+				whiteoutEntry("d3/f1"),
+				fileEntry("d3/f2", []byte("content"), 0644),
+				dirEntry("d4/", 0755),
+				fileEntry("d4/f0", []byte("content"), 0644),
+				whiteoutEntry("d4/f1"),
+				whiteoutEntry("d5"),
+			},
+			a: fstest.Apply(
+				fstest.CreateDir("/d1/", 0755),
+				fstest.CreateFile("/d1/f1", []byte("content"), 0644),
+				fstest.CreateDir("/d2/", 0755),
+				fstest.CreateFile("/d2/f1", []byte("content"), 0644),
+				fstest.CreateFile("/d2/f2", []byte("content"), 0644),
+				fstest.CreateDir("/d3/", 0755),
+				fstest.CreateFile("/d3/f1", []byte("content"), 0644),
+				fstest.CreateDir("/d4/", 0755),
+				fstest.CreateFile("/d4/f1", []byte("content"), 0644),
+				fstest.CreateDir("/d5/", 0755),
+				fstest.CreateFile("/d5/f1", []byte("content"), 0644),
+			),
+			b: fstest.Apply(
+				fstest.Remove("/d1/f1"),
+				fstest.Remove("/d2/f1"),
+				fstest.Chmod("/d2/f2", 0777),
+				fstest.Remove("/d3/f1"),
+				fstest.CreateFile("/d3/f2", []byte("content"), 0644),
+				fstest.Remove("/d4/f1"),
+				fstest.CreateFile("/d4/f0", []byte("content"), 0644),
+				fstest.RemoveAll("/d5"),
+			),
+		},
 	}
 
 	for _, at := range tests {