diff --git a/src/os/file_windows.go b/src/os/file_windows.go
index 0d8c0fd20d..cc695fd94c 100644
--- a/src/os/file_windows.go
+++ b/src/os/file_windows.go
@@ -330,8 +330,18 @@ func Symlink(oldname, newname string) error {
 
 	// need the exact location of the oldname when it's relative to determine if it's a directory
 	destpath := oldname
-	if !isAbs(oldname) {
-		destpath = dirname(newname) + `\` + oldname
+	if v := volumeName(oldname); v == "" {
+		if len(oldname) > 0 && IsPathSeparator(oldname[0]) {
+			// oldname is relative to the volume containing newname.
+			if v = volumeName(newname); v != "" {
+				// Prepend the volume explicitly, because it may be different from the
+				// volume of the current working directory.
+				destpath = v + oldname
+			}
+		} else {
+			// oldname is relative to newname.
+			destpath = dirname(newname) + `\` + oldname
+		}
 	}
 
 	fi, err := Stat(destpath)
diff --git a/src/os/os_windows_test.go b/src/os/os_windows_test.go
index 8c14103143..f03ec750d0 100644
--- a/src/os/os_windows_test.go
+++ b/src/os/os_windows_test.go
@@ -965,9 +965,10 @@ func TestWindowsDevNullFile(t *testing.T) {
 // works on Windows when developer mode is active.
 // This is supported starting Windows 10 (1703, v10.0.14972).
 func TestSymlinkCreation(t *testing.T) {
-	if !isWindowsDeveloperModeActive() {
+	if !testenv.HasSymlink() && !isWindowsDeveloperModeActive() {
 		t.Skip("Windows developer mode is not active")
 	}
+	t.Parallel()
 
 	temp, err := ioutil.TempDir("", "TestSymlinkCreation")
 	if err != nil {
@@ -1005,6 +1006,122 @@ func isWindowsDeveloperModeActive() bool {
 	return val != 0
 }
 
+// TestRootRelativeDirSymlink verifies that symlinks to paths relative to the
+// drive root (beginning with "\" but no volume name) are created with the
+// correct symlink type.
+// (See https://golang.org/issue/39183#issuecomment-632175728.)
+func TestRootRelativeDirSymlink(t *testing.T) {
+	testenv.MustHaveSymlink(t)
+	t.Parallel()
+
+	temp := t.TempDir()
+	dir := filepath.Join(temp, "dir")
+	if err := os.Mkdir(dir, 0755); err != nil {
+		t.Fatal(err)
+	}
+
+	volumeRelDir := strings.TrimPrefix(dir, filepath.VolumeName(dir)) // leaves leading backslash
+
+	link := filepath.Join(temp, "link")
+	err := os.Symlink(volumeRelDir, link)
+	if err != nil {
+		t.Fatal(err)
+	}
+	t.Logf("Symlink(%#q, %#q)", volumeRelDir, link)
+
+	f, err := os.Open(link)
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer f.Close()
+	if fi, err := f.Stat(); err != nil {
+		t.Fatal(err)
+	} else if !fi.IsDir() {
+		t.Errorf("Open(%#q).Stat().IsDir() = false; want true", f.Name())
+	}
+}
+
+// TestWorkingDirectoryRelativeSymlink verifies that symlinks to paths relative
+// to the current working directory for the drive, such as "C:File.txt", are
+// correctly converted to absolute links of the correct symlink type (per
+// https://docs.microsoft.com/en-us/windows/win32/fileio/creating-symbolic-links).
+func TestWorkingDirectoryRelativeSymlink(t *testing.T) {
+	testenv.MustHaveSymlink(t)
+
+	// Construct a directory to be symlinked.
+	temp := t.TempDir()
+	if v := filepath.VolumeName(temp); len(v) < 2 || v[1] != ':' {
+		t.Skipf("Can't test relative symlinks: t.TempDir() (%#q) does not begin with a drive letter.", temp)
+	}
+
+	absDir := filepath.Join(temp, `dir\sub`)
+	if err := os.MkdirAll(absDir, 0755); err != nil {
+		t.Fatal(err)
+	}
+
+	// Change to the temporary directory and construct a
+	// working-directory-relative symlink.
+	oldwd, err := os.Getwd()
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer func() {
+		if err := os.Chdir(oldwd); err != nil {
+			t.Fatal(err)
+		}
+	}()
+	if err := os.Chdir(temp); err != nil {
+		t.Fatal(err)
+	}
+	t.Logf("Chdir(%#q)", temp)
+
+	wdRelDir := filepath.VolumeName(temp) + `dir\sub` // no backslash after volume.
+	absLink := filepath.Join(temp, "link")
+	err = os.Symlink(wdRelDir, absLink)
+	if err != nil {
+		t.Fatal(err)
+	}
+	t.Logf("Symlink(%#q, %#q)", wdRelDir, absLink)
+
+	// Now change back to the original working directory and verify that the
+	// symlink still refers to its original path and is correctly marked as a
+	// directory.
+	if err := os.Chdir(oldwd); err != nil {
+		t.Fatal(err)
+	}
+	t.Logf("Chdir(%#q)", oldwd)
+
+	resolved, err := os.Readlink(absLink)
+	if err != nil {
+		t.Errorf("Readlink(%#q): %v", absLink, err)
+	} else if resolved != absDir {
+		t.Errorf("Readlink(%#q) = %#q; want %#q", absLink, resolved, absDir)
+	}
+
+	linkFile, err := os.Open(absLink)
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer linkFile.Close()
+
+	linkInfo, err := linkFile.Stat()
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !linkInfo.IsDir() {
+		t.Errorf("Open(%#q).Stat().IsDir() = false; want true", absLink)
+	}
+
+	absInfo, err := os.Stat(absDir)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	if !os.SameFile(absInfo, linkInfo) {
+		t.Errorf("SameFile(Stat(%#q), Open(%#q).Stat()) = false; want true", absDir, absLink)
+	}
+}
+
 // TestStatOfInvalidName is regression test for issue #24999.
 func TestStatOfInvalidName(t *testing.T) {
 	_, err := os.Stat("*.go")