diff --git a/compat/win32/git-wrapper.c b/compat/win32/git-wrapper.c
index 3f8a5b31415f2b..c2e758039f305d 100644
--- a/compat/win32/git-wrapper.c
+++ b/compat/win32/git-wrapper.c
@@ -37,7 +37,7 @@ static void print_error(LPCWSTR prefix, DWORD error_number)
 	LocalFree((HLOCAL)buffer);
 }
 
-static void setup_environment(LPWSTR exepath, int full_path)
+static void setup_environment(LPWSTR top_level_path, int full_path)
 {
 	WCHAR msystem[64];
 	LPWSTR path2 = NULL;
@@ -90,7 +90,7 @@ static void setup_environment(LPWSTR exepath, int full_path)
 	len = GetEnvironmentVariable(L"PATH", NULL, 0);
 	len = sizeof(WCHAR) * (len + 2 * MAX_PATH);
 	path2 = (LPWSTR)malloc(len);
-	wcscpy(path2, exepath);
+	wcscpy(path2, top_level_path);
 	if (!full_path)
 		PathAppend(path2, L"cmd;");
 	else {
@@ -98,14 +98,14 @@ static void setup_environment(LPWSTR exepath, int full_path)
 		if (_waccess(path2, 0) != -1) {
 			/* We are in an MSys2-based setup */
 			wcscat(path2, L";");
-			wcscat(path2, exepath);
+			wcscat(path2, top_level_path);
 			PathAppend(path2, L"usr\\bin;");
 		}
 		else {
 			/* Fall back to MSys1 paths */
-			wcscpy(path2, exepath);
+			wcscpy(path2, top_level_path);
 			PathAppend(path2, L"bin;");
-			wcscat(path2, exepath);
+			wcscat(path2, top_level_path);
 			PathAppend(path2, L"mingw\\bin;");
 		}
 	}
@@ -422,18 +422,59 @@ static int configure_via_resource(LPWSTR basename, LPWSTR exepath, LPWSTR exep,
 	return 1;
 }
 
+static void initialize_top_level_path(LPWSTR top_level_path, LPWSTR exepath,
+		LPWSTR msystem_bin, int strip_count)
+{
+	wcscpy(top_level_path, exepath);
+
+	while (strip_count) {
+		if (strip_count < 0) {
+			int len = wcslen(top_level_path);
+			PathAppend(top_level_path, msystem_bin);
+			if (_waccess(top_level_path, 0) != -1) {
+				/* We are in an MSys2-based setup */
+				top_level_path[len] = L'\0';
+				return;
+			}
+			top_level_path[len] = L'\0';
+			PathAppend(top_level_path, L"mingw\\bin");
+			if (_waccess(top_level_path, 0) != -1) {
+				/* We are in an MSys-based setup */
+				top_level_path[len] = L'\0';
+				return;
+			}
+			top_level_path[len] = L'\0';
+			if (!(++strip_count)) {
+				fwprintf(stderr, L"Top-level not found: %s\n",
+					exepath);
+				exit(1);
+			}
+		}
+
+		if (!PathRemoveFileSpec(top_level_path)) {
+			fwprintf(stderr, L"Invalid executable path: %s\n",
+					exepath);
+			ExitProcess(1);
+		}
+
+		if (strip_count > 0)
+			--strip_count;
+	}
+}
+
 int main(void)
 {
 	int r = 1, wait = 1, prefix_args_len = -1, needs_env_setup = 1,
 		is_git_command = 1, full_path = 1, skip_arguments = 0,
 		allocate_console = 0, show_console = 0;
-	WCHAR exepath[MAX_PATH], exe[MAX_PATH];
+	WCHAR exepath[MAX_PATH], exe[MAX_PATH], top_level_path[MAX_PATH];
 	LPWSTR cmd = NULL, exep = exe, prefix_args = NULL, basename;
 	LPWSTR working_directory = NULL;
 
 	/* Determine MSys2-based Git path. */
 	swprintf(msystem_bin, sizeof(msystem_bin),
 		L"mingw%d\\bin", (int) sizeof(void *) * 8);
+	*top_level_path = L'\0';
 
 	/* get the installation location */
 	GetModuleFileName(NULL, exepath, MAX_PATH);
@@ -453,25 +494,23 @@ int main(void)
 		static WCHAR buffer[BUFSIZE];
 		wait = 0;
 		allocate_console = 1;
-		if (!PathRemoveFileSpec(exepath)) {
-			fwprintf(stderr,
-				L"Invalid executable path: %s\n", exepath);
-			ExitProcess(1);
-		}
+		initialize_top_level_path(top_level_path, exepath, NULL, 1);
 
 		/* set the default exe module */
-		wcscpy(exe, exepath);
+		wcscpy(exe, top_level_path);
 		PathAppend(exe, msystem_bin);
 		PathAppend(exe, L"wish.exe");
 		if (_waccess(exe, 0) != -1)
 			swprintf(buffer, BUFSIZE,
 				L"\"%s\\%.*s\\libexec\\git-core\"",
-				exepath, wcslen(msystem_bin) - 4, msystem_bin);
+				top_level_path,
+				wcslen(msystem_bin) - 4, msystem_bin);
 		else {
-			wcscpy(exe, exepath);
+			wcscpy(exe, top_level_path);
 			PathAppend(exe, L"mingw\\bin\\wish.exe");
 			swprintf(buffer, BUFSIZE,
-				L"\"%s\\mingw\\libexec\\git-core\"", exepath);
+				L"\"%s\\mingw\\libexec\\git-core\"",
+				top_level_path);
 		}
 		PathAppend(buffer, L"git-gui");
 		prefix_args = buffer;
@@ -491,39 +530,31 @@ int main(void)
 		PathAppend(exe, L"git.exe");
 	}
 	else if (!wcsicmp(basename, L"git.exe")) {
-		if (!PathRemoveFileSpec(exepath)) {
-			fwprintf(stderr,
-				L"Invalid executable path: %s\n", exepath);
-			ExitProcess(1);
-		}
+		initialize_top_level_path(top_level_path, exepath, NULL, 1);
 
 		/* set the default exe module */
-		wcscpy(exe, exepath);
+		wcscpy(exe, top_level_path);
 		PathAppend(exe, msystem_bin);
 		PathAppend(exe, L"git.exe");
 		if (_waccess(exe, 0) == -1) {
-			wcscpy(exe, exepath);
+			wcscpy(exe, top_level_path);
 			PathAppend(exe, L"bin\\git.exe");
 		}
 	}
 	else if (!wcsicmp(basename, L"gitk.exe")) {
 		static WCHAR buffer[BUFSIZE];
 		allocate_console = 1;
-		if (!PathRemoveFileSpec(exepath)) {
-			fwprintf(stderr,
-				L"Invalid executable path: %s\n", exepath);
-			ExitProcess(1);
-		}
+		initialize_top_level_path(top_level_path, exepath, NULL, 1);
 
 		/* set the default exe module */
-		wcscpy(exe, exepath);
-		swprintf(buffer, BUFSIZE, L"\"%s\"", exepath);
+		wcscpy(exe, top_level_path);
+		swprintf(buffer, BUFSIZE, L"\"%s\"", top_level_path);
 		PathAppend(exe, msystem_bin);
 		PathAppend(exe, L"wish.exe");
 		if (_waccess(exe, 0) != -1)
 			PathAppend(buffer, msystem_bin);
 		else {
-			wcscpy(exe, exepath);
+			wcscpy(exe, top_level_path);
 			PathAppend(exe, L"mingw\\bin\\wish.exe");
 			PathAppend(buffer, L"mingw\\bin");
 		}
@@ -532,8 +563,13 @@ int main(void)
 		prefix_args_len = wcslen(buffer);
 	}
 
-	if (needs_env_setup)
-		setup_environment(exepath, full_path);
+	if (needs_env_setup) {
+		if (!top_level_path[0])
+			initialize_top_level_path(top_level_path, exepath,
+					msystem_bin, -4);
+
+		setup_environment(top_level_path, full_path);
+	}
 	cmd = fixup_commandline(exepath, &exep, &wait,
 		prefix_args, prefix_args_len, is_git_command, skip_arguments);