diff --git a/Documentation/config/safe.txt b/Documentation/config/safe.txt
index fa02f3ccc5..ec9c85c8f8 100644
--- a/Documentation/config/safe.txt
+++ b/Documentation/config/safe.txt
@@ -40,3 +40,9 @@ which id the original user has.
 If that is not what you would prefer and want git to only trust
 repositories that are owned by root instead, then you can remove
 the `SUDO_UID` variable from root's environment before invoking git.
++
+Due to the permission model on Windows where ACLs are used instead of
+Unix' simpler permission model, it can be a bit tricky to figure out why
+a directory is considered unsafe. To help with this, Git will provide
+more detailed information when the environment variable
+`GIT_TEST_DEBUG_UNSAFE_DIRECTORIES` is set to `true`.
diff --git a/compat/mingw.c b/compat/mingw.c
index 2781447693..8a9ad3fdaf 100644
--- a/compat/mingw.c
+++ b/compat/mingw.c
@@ -1,6 +1,7 @@
 #include "../git-compat-util.h"
 #include "win32.h"
 #include <aclapi.h>
+#include <sddl.h>
 #include <conio.h>
 #include <wchar.h>
 #include "../strbuf.h"
@@ -3028,6 +3029,7 @@ int is_path_owned_by_current_sid(const char *path)
 	else if (sid && IsValidSid(sid)) {
 		/* Now, verify that the SID matches the current user's */
 		static PSID current_user_sid;
+		BOOL is_member;
 
 		if (!current_user_sid)
 			current_user_sid = get_current_user_sid();
@@ -3036,6 +3038,35 @@ int is_path_owned_by_current_sid(const char *path)
 		    IsValidSid(current_user_sid) &&
 		    EqualSid(sid, current_user_sid))
 			result = 1;
+		else if (IsWellKnownSid(sid, WinBuiltinAdministratorsSid) &&
+			 CheckTokenMembership(NULL, sid, &is_member) &&
+			 is_member)
+			/*
+			 * If owned by the Administrators group, and the
+			 * current user is an administrator, we consider that
+			 * okay, too.
+			 */
+			result = 1;
+		else if (git_env_bool("GIT_TEST_DEBUG_UNSAFE_DIRECTORIES", 0)) {
+			LPSTR str1, str2, to_free1 = NULL, to_free2 = NULL;
+
+			if (ConvertSidToStringSidA(sid, &str1))
+				to_free1 = str1;
+			else
+				str1 = "(inconvertible)";
+
+			if (!current_user_sid)
+				str2 = "(none)";
+			else if (!IsValidSid(current_user_sid))
+				str2 = "(invalid)";
+			else if (ConvertSidToStringSidA(current_user_sid, &str2))
+				to_free2 = str2;
+			else
+				str2 = "(inconvertible)";
+			warning("'%s' is owned by:\n\t'%s'\nbut the current user is:\n\t'%s'", path, str1, str2);
+			LocalFree(to_free1);
+			LocalFree(to_free2);
+		}
 	}
 
 	/*