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 b5502997e2..e8e90ae02d 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"
@@ -2717,6 +2718,26 @@ int is_path_owned_by_current_sid(const char *path)
 		    IsValidSid(current_user_sid) &&
 		    EqualSid(sid, current_user_sid))
 			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);
+		}
 	}
 
 	/*
diff --git a/setup.c b/setup.c
index 09b6549ba9..c5ef2cc074 100644
--- a/setup.c
+++ b/setup.c
@@ -1433,13 +1433,23 @@ const char *setup_git_directory_gently(int *nongit_ok)
 	case GIT_DIR_INVALID_OWNERSHIP:
 		if (!nongit_ok) {
 			struct strbuf quoted = STRBUF_INIT;
+			struct strbuf hint = STRBUF_INIT;
+
+#ifdef __MINGW32__
+			if (!git_env_bool("GIT_TEST_DEBUG_UNSAFE_DIRECTORIES", 0))
+				strbuf_addstr(&hint,
+					      _("\n\nSet the environment variable "
+						"GIT_TEST_DEBUG_UNSAFE_DIRECTORIES=true "
+						"and run\n"
+						"again for more information."));
+#endif
 
 			sq_quote_buf_pretty(&quoted, dir.buf);
 			die(_("detected dubious ownership in repository at '%s'\n"
 			      "To add an exception for this directory, call:\n"
 			      "\n"
-			      "\tgit config --global --add safe.directory %s"),
-			    dir.buf, quoted.buf);
+			      "\tgit config --global --add safe.directory %s%s"),
+			    dir.buf, quoted.buf, hint.buf);
 		}
 		*nongit_ok = 1;
 		break;