diff --git a/archive/tar.go b/archive/tar.go
index fa9601c69..99cfc35fc 100644
--- a/archive/tar.go
+++ b/archive/tar.go
@@ -395,6 +395,7 @@ type changeWriter struct {
 	whiteoutT time.Time
 	inodeSrc  map[uint64]string
 	inodeRefs map[uint64][]string
+	addedDirs map[string]struct{}
 }
 
 func newChangeWriter(w io.Writer, source string) *changeWriter {
@@ -404,6 +405,7 @@ func newChangeWriter(w io.Writer, source string) *changeWriter {
 		whiteoutT: time.Now(),
 		inodeSrc:  map[uint64]string{},
 		inodeRefs: map[uint64][]string{},
+		addedDirs: map[string]struct{}{},
 	}
 }
 
@@ -416,6 +418,7 @@ func (cw *changeWriter) HandleChange(k fs.ChangeKind, p string, f os.FileInfo, e
 		whiteOutBase := filepath.Base(p)
 		whiteOut := filepath.Join(whiteOutDir, whiteoutPrefix+whiteOutBase)
 		hdr := &tar.Header{
+			Typeflag:   tar.TypeReg,
 			Name:       whiteOut[1:],
 			Size:       0,
 			ModTime:    cw.whiteoutT,
@@ -485,10 +488,8 @@ func (cw *changeWriter) HandleChange(k fs.ChangeKind, p string, f os.FileInfo, e
 				additionalLinks = cw.inodeRefs[inode]
 				delete(cw.inodeRefs, inode)
 			}
-		} else if k == fs.ChangeKindUnmodified && !f.IsDir() {
+		} else if k == fs.ChangeKindUnmodified {
 			// Nothing to write to diff
-			// Unmodified directories should still be written to keep
-			// directory permissions correct on direct unpack
 			return nil
 		}
 
@@ -501,6 +502,9 @@ func (cw *changeWriter) HandleChange(k fs.ChangeKind, p string, f os.FileInfo, e
 			hdr.PAXRecords[paxSchilyXattr+"security.capability"] = string(capability)
 		}
 
+		if err := cw.includeParents(hdr); err != nil {
+			return err
+		}
 		if err := cw.tw.WriteHeader(hdr); err != nil {
 			return errors.Wrap(err, "failed to write file header")
 		}
@@ -530,6 +534,10 @@ func (cw *changeWriter) HandleChange(k fs.ChangeKind, p string, f os.FileInfo, e
 				hdr.Typeflag = tar.TypeLink
 				hdr.Linkname = source
 				hdr.Size = 0
+
+				if err := cw.includeParents(hdr); err != nil {
+					return err
+				}
 				if err := cw.tw.WriteHeader(hdr); err != nil {
 					return errors.Wrap(err, "failed to write file header")
 				}
@@ -546,6 +554,29 @@ func (cw *changeWriter) Close() error {
 	return nil
 }
 
+func (cw *changeWriter) includeParents(hdr *tar.Header) error {
+	name := strings.TrimRight(hdr.Name, "/")
+	fname := filepath.Join(cw.source, name)
+	parent := filepath.Dir(name)
+	pname := filepath.Join(cw.source, parent)
+
+	// Do not include root directory as parent
+	if fname != cw.source && pname != cw.source {
+		_, ok := cw.addedDirs[parent]
+		if !ok {
+			cw.addedDirs[parent] = struct{}{}
+			fi, err := os.Stat(pname)
+			if err != nil {
+				return err
+			}
+			if err := cw.HandleChange(fs.ChangeKindModify, parent, fi, nil); err != nil {
+				return err
+			}
+		}
+	}
+	return nil
+}
+
 func copyBuffered(ctx context.Context, dst io.Writer, src io.Reader) (written int64, err error) {
 	buf := bufferPool.Get().(*[]byte)
 	defer bufferPool.Put(buf)
diff --git a/archive/tar_test.go b/archive/tar_test.go
index 276a47d00..d5e10a6c6 100644
--- a/archive/tar_test.go
+++ b/archive/tar_test.go
@@ -698,6 +698,44 @@ func TestDiffTar(t *testing.T) {
 				fstest.CreateFile("/d2/f", []byte("ok"), 0644),
 			),
 		},
+		{
+			name: "HardlinkParentInclusion",
+			validators: []tarEntryValidator{
+				dirEntry("d2/", 0755),
+				fileEntry("d2/l1", []byte("link me"), 0644),
+				// d1/f1 and its parent is included after the new link,
+				// before the new link was included, these files would
+				// not habe needed
+				dirEntry("d1/", 0755),
+				linkEntry("d1/f1", "d2/l1"),
+				dirEntry("d3/", 0755),
+				fileEntry("d3/l1", []byte("link me"), 0644),
+				dirEntry("d4/", 0755),
+				linkEntry("d4/f1", "d3/l1"),
+				whiteoutEntry("d6/l1"),
+				whiteoutEntry("d6/l2"),
+			},
+			a: fstest.Apply(
+				fstest.CreateDir("/d1/", 0755),
+				fstest.CreateFile("/d1/f1", []byte("link me"), 0644),
+				fstest.CreateDir("/d2/", 0755),
+				fstest.CreateFile("/d2/f1", []byte("link me"), 0644),
+				fstest.CreateDir("/d3/", 0755),
+				fstest.CreateDir("/d4/", 0755),
+				fstest.CreateFile("/d4/f1", []byte("link me"), 0644),
+				fstest.CreateDir("/d5/", 0755),
+				fstest.CreateFile("/d5/f1", []byte("link me"), 0644),
+				fstest.CreateDir("/d6/", 0755),
+				fstest.Link("/d1/f1", "/d6/l1"),
+				fstest.Link("/d5/f1", "/d6/l2"),
+			),
+			b: fstest.Apply(
+				fstest.Link("/d1/f1", "/d2/l1"),
+				fstest.Link("/d4/f1", "/d3/l1"),
+				fstest.Remove("/d6/l1"),
+				fstest.Remove("/d6/l2"),
+			),
+		},
 	}
 
 	for _, at := range tests {
@@ -740,6 +778,37 @@ func fileEntry(name string, expected []byte, mode int) tarEntryValidator {
 	}
 }
 
+func linkEntry(name, link string) tarEntryValidator {
+	return func(hdr *tar.Header, b []byte) error {
+		if hdr.Typeflag != tar.TypeLink {
+			return errors.New("not link type")
+		}
+		if hdr.Name != name {
+			return errors.Errorf("wrong name %q, expected %q", hdr.Name, name)
+		}
+		if hdr.Linkname != link {
+			return errors.Errorf("wrong link %q, expected %q", hdr.Linkname, link)
+		}
+		return nil
+	}
+}
+
+func whiteoutEntry(name string) tarEntryValidator {
+	whiteOutDir := filepath.Dir(name)
+	whiteOutBase := filepath.Base(name)
+	whiteOut := filepath.Join(whiteOutDir, whiteoutPrefix+whiteOutBase)
+
+	return func(hdr *tar.Header, b []byte) error {
+		if hdr.Typeflag != tar.TypeReg {
+			return errors.Errorf("not file type: %q", hdr.Typeflag)
+		}
+		if hdr.Name != whiteOut {
+			return errors.Errorf("wrong name %q, expected whiteout %q", hdr.Name, name)
+		}
+		return nil
+	}
+}
+
 func makeDiffTarTest(validators []tarEntryValidator, a, b fstest.Applier) func(*testing.T) {
 	return func(t *testing.T) {
 		ad, err := ioutil.TempDir("", "test-make-diff-tar-")