diff --git a/compat/mingw.c b/compat/mingw.c
index 8b7b526d9f6fa6..41831e88163ee2 100644
--- a/compat/mingw.c
+++ b/compat/mingw.c
@@ -3851,7 +3851,12 @@ int handle_long_path(wchar_t *path, int len, int max_path, int expand)
 	 * "cwd + path" doesn't due to '..' components)
 	 */
 	if (result < max_path) {
-		wcscpy(path, buf);
+		/* Be careful not to add a drive prefix if there was none */
+		if (is_wdir_sep(path[0]) &&
+		    !is_wdir_sep(buf[0]) && buf[1] == L':' && is_wdir_sep(buf[2]))
+			wcscpy(path, buf + 2);
+		else
+			wcscpy(path, buf);
 		return result;
 	}
 
diff --git a/t/t2031-checkout-long-paths.sh b/t/t2031-checkout-long-paths.sh
index f30f8920ca689c..15416a1d6ee8c7 100755
--- a/t/t2031-checkout-long-paths.sh
+++ b/t/t2031-checkout-long-paths.sh
@@ -99,4 +99,13 @@ test_expect_success SHORTABSPATH 'clean up path close to MAX_PATH' '
 	test ! -d "$subdir1"
 '
 
+test_expect_success SYMLINKS_WINDOWS 'leave drive-less, short paths intact' '
+	printf "/Program Files" >symlink-target &&
+	symlink_target_oid="$(git hash-object -w --stdin <symlink-target)" &&
+	git update-index --add --cacheinfo 120000,$symlink_target_oid,PF &&
+	git -c core.symlinks=true checkout -- PF &&
+	cmd //c dir >actual &&
+	grep "<SYMLINKD\\?> *PF *\\[\\\\Program Files\\]" actual
+'
+
 test_done