diff --git a/builder/remotecontext/tarsum_test.go b/builder/remotecontext/tarsum_test.go
index fd5d9edc2f..64b7f1d5f2 100644
--- a/builder/remotecontext/tarsum_test.go
+++ b/builder/remotecontext/tarsum_test.go
@@ -60,7 +60,7 @@ func TestHashFile(t *testing.T) {
 		t.Fatalf("Hash returned empty sum")
 	}
 
-	expected := "1149ab94af7be6cc1da1335e398f24ee1cf4926b720044d229969dfc248ae7ec"
+	expected := "55dfeb344351ab27f59aa60ebb0ed12025a2f2f4677bf77d26ea7a671274a9ca"
 
 	if actual := sum; expected != actual {
 		t.Fatalf("invalid checksum. expected %s, got %s", expected, actual)
@@ -97,7 +97,7 @@ func TestHashSubdir(t *testing.T) {
 		t.Fatalf("Hash returned empty sum")
 	}
 
-	expected := "d7f8d6353dee4816f9134f4156bf6a9d470fdadfb5d89213721f7e86744a4e69"
+	expected := "74a3326b8e766ce63a8e5232f22e9dd895be647fb3ca7d337e5e0a9b3da8ef28"
 
 	if actual := sum; expected != actual {
 		t.Fatalf("invalid checksum. expected %s, got %s", expected, actual)
diff --git a/pkg/archive/archive.go b/pkg/archive/archive.go
index 6d8464b60b..bd8ce64a0b 100644
--- a/pkg/archive/archive.go
+++ b/pkg/archive/archive.go
@@ -99,16 +99,6 @@ const (
 	OverlayWhiteoutFormat
 )
 
-const (
-	modeISDIR  = 040000  // Directory
-	modeISFIFO = 010000  // FIFO
-	modeISREG  = 0100000 // Regular file
-	modeISLNK  = 0120000 // Symbolic link
-	modeISBLK  = 060000  // Block special file
-	modeISCHR  = 020000  // Character special file
-	modeISSOCK = 0140000 // Socket
-)
-
 // IsArchivePath checks if the (possibly compressed) file at the given path
 // starts with a tar file header.
 func IsArchivePath(path string) bool {
@@ -458,9 +448,7 @@ func FileInfoHeaderNoLookups(fi os.FileInfo, link string) (*tar.Header, error) {
 // but is safe to call from a chrooted process. The AccessTime and ChangeTime
 // fields are not set in the returned header, ModTime is truncated to one-second
 // precision, and the Uname and Gname fields are only set when fi is a FileInfo
-// value returned from tar.Header.FileInfo(). Also, regardless of Go version,
-// this function fills file type bits (e.g. hdr.Mode |= modeISDIR), which have
-// been deleted since Go 1.9 archive/tar.
+// value returned from tar.Header.FileInfo().
 func FileInfoHeader(name string, fi os.FileInfo, link string) (*tar.Header, error) {
 	hdr, err := FileInfoHeaderNoLookups(fi, link)
 	if err != nil {
@@ -470,36 +458,11 @@ func FileInfoHeader(name string, fi os.FileInfo, link string) (*tar.Header, erro
 	hdr.ModTime = hdr.ModTime.Truncate(time.Second)
 	hdr.AccessTime = time.Time{}
 	hdr.ChangeTime = time.Time{}
-	hdr.Mode = fillGo18FileTypeBits(int64(chmodTarEntry(os.FileMode(hdr.Mode))), fi)
+	hdr.Mode = int64(chmodTarEntry(os.FileMode(hdr.Mode)))
 	hdr.Name = canonicalTarName(name, fi.IsDir())
 	return hdr, nil
 }
 
-// fillGo18FileTypeBits fills type bits which have been removed on Go 1.9 archive/tar
-// https://github.com/golang/go/commit/66b5a2f
-func fillGo18FileTypeBits(mode int64, fi os.FileInfo) int64 {
-	fm := fi.Mode()
-	switch {
-	case fm.IsRegular():
-		mode |= modeISREG
-	case fi.IsDir():
-		mode |= modeISDIR
-	case fm&os.ModeSymlink != 0:
-		mode |= modeISLNK
-	case fm&os.ModeDevice != 0:
-		if fm&os.ModeCharDevice != 0 {
-			mode |= modeISCHR
-		} else {
-			mode |= modeISBLK
-		}
-	case fm&os.ModeNamedPipe != 0:
-		mode |= modeISFIFO
-	case fm&os.ModeSocket != 0:
-		mode |= modeISSOCK
-	}
-	return mode
-}
-
 // ReadSecurityXattrToTarHeader reads security.capability xattr from filesystem
 // to a tar header
 func ReadSecurityXattrToTarHeader(path string, hdr *tar.Header) error {
diff --git a/pkg/archive/archive_windows.go b/pkg/archive/archive_windows.go
index 7260174bfb..da268f89c2 100644
--- a/pkg/archive/archive_windows.go
+++ b/pkg/archive/archive_windows.go
@@ -31,14 +31,11 @@ func CanonicalTarNameForPath(p string) string {
 // chmodTarEntry is used to adjust the file permissions used in tar header based
 // on the platform the archival is done.
 func chmodTarEntry(perm os.FileMode) os.FileMode {
-	// perm &= 0755 // this 0-ed out tar flags (like link, regular file, directory marker etc.)
-	permPart := perm & os.ModePerm
-	noPermPart := perm &^ os.ModePerm
-	// Add the x bit: make everything +x from windows
-	permPart |= 0111
-	permPart &= 0755
+	// Remove group- and world-writable bits.
+	perm &= 0o755
 
-	return noPermPart | permPart
+	// Add the x bit: make everything +x on Windows
+	return perm | 0o111
 }
 
 func setHeaderForSpecialDevice(hdr *tar.Header, name string, stat interface{}) (err error) {
diff --git a/pkg/archive/archive_windows_test.go b/pkg/archive/archive_windows_test.go
index f03b1e2d82..8f8eb03545 100644
--- a/pkg/archive/archive_windows_test.go
+++ b/pkg/archive/archive_windows_test.go
@@ -75,8 +75,6 @@ func TestChmodTarEntry(t *testing.T) {
 		{0644, 0755},
 		{0755, 0755},
 		{0444, 0555},
-		{0755 | os.ModeDir, 0755 | os.ModeDir},
-		{0755 | os.ModeSymlink, 0755 | os.ModeSymlink},
 	}
 	for _, v := range cases {
 		if out := chmodTarEntry(v.in); out != v.expected {