diff --git a/Makefile b/Makefile
index 93dc4948d3..fa1a02289c 100644
--- a/Makefile
+++ b/Makefile
@@ -72,6 +72,9 @@ all:
 # Define NO_FAST_WORKING_DIRECTORY if accessing objects in pack files is
 # generally faster on your platform than accessing the working directory.
 #
+# Define NO_TRUSTABLE_FILEMODE if your filesystem may claim to support
+# the executable mode bit, but doesn't really do so.
+#
 # Define NO_IPV6 if you lack IPv6 support and getaddrinfo().
 #
 # Define NO_SOCKADDR_STORAGE if your platform does not have struct
@@ -361,6 +364,7 @@ ifeq ($(uname_O),Cygwin)
 	NEEDS_LIBICONV = YesPlease
 	NO_C99_FORMAT = YesPlease
 	NO_FAST_WORKING_DIRECTORY = UnfortunatelyYes
+	NO_TRUSTABLE_FILEMODE = UnfortunatelyYes
 	# There are conflicting reports about this.
 	# On some boxes NO_MMAP is needed, and not so elsewhere.
 	# Try commenting this out if you suspect MMAP is more efficient
@@ -521,6 +525,9 @@ endif
 ifdef NO_FAST_WORKING_DIRECTORY
 	BASIC_CFLAGS += -DNO_FAST_WORKING_DIRECTORY
 endif
+ifdef NO_TRUSTABLE_FILEMODE
+	BASIC_CFLAGS += -DNO_TRUSTABLE_FILEMODE
+endif
 ifdef NO_IPV6
 	BASIC_CFLAGS += -DNO_IPV6
 endif
diff --git a/builtin-init-db.c b/builtin-init-db.c
index 01f366ad0b..97fd82ff06 100644
--- a/builtin-init-db.c
+++ b/builtin-init-db.c
@@ -10,6 +10,12 @@
 #define DEFAULT_GIT_TEMPLATE_DIR "/usr/share/git-core/templates/"
 #endif
 
+#ifdef NO_TRUSTABLE_FILEMODE
+#define TEST_FILEMODE 0
+#else
+#define TEST_FILEMODE 1
+#endif
+
 static void safe_create_dir(const char *dir, int share)
 {
 	if (mkdir(dir, 0777) < 0) {
@@ -175,6 +181,7 @@ static int create_default_files(const char *git_dir, const char *template_path)
 	struct stat st1;
 	char repo_version_string[10];
 	int reinit;
+	int filemode;
 
 	if (len > sizeof(path)-50)
 		die("insane git directory %s", git_dir);
@@ -236,14 +243,14 @@ static int create_default_files(const char *git_dir, const char *template_path)
 	strcpy(path + len, "config");
 
 	/* Check filemode trustability */
-	if (!lstat(path, &st1)) {
+	filemode = TEST_FILEMODE;
+	if (TEST_FILEMODE && !lstat(path, &st1)) {
 		struct stat st2;
-		int filemode = (!chmod(path, st1.st_mode ^ S_IXUSR) &&
+		filemode = (!chmod(path, st1.st_mode ^ S_IXUSR) &&
 				!lstat(path, &st2) &&
 				st1.st_mode != st2.st_mode);
-		git_config_set("core.filemode",
-			       filemode ? "true" : "false");
 	}
+	git_config_set("core.filemode", filemode ? "true" : "false");
 
 	/* Enable logAllRefUpdates if a working tree is attached */
 	if (!is_bare_git_dir(git_dir))