diff --git a/src/fileops.c b/src/fileops.c
index cd4b3c42a..95a65893c 100644
--- a/src/fileops.c
+++ b/src/fileops.c
@@ -417,11 +417,17 @@ int git_futils_find_system_file(git_buf *path, const char *filename)
 	struct win32_path root;
 
 	if (win32_expand_path(&root, L"%PROGRAMFILES%\\Git\\etc\\") < 0 ||
-		win32_find_file(path, &root, filename) < 0) {
-		giterr_set(GITERR_OS, "Cannot find the system's Program Files directory");
+		root.path[0] == L'%') /* i.e. no expansion happened */
+	{
+		giterr_set(GITERR_OS, "Cannot locate the system's Program Files directory");
 		return -1;
 	}
 
+	if (win32_find_file(path, &root, filename) < 0) {
+		git_buf_clear(path);
+		return GIT_ENOTFOUND;
+	}
+
 	return 0;
 
 #else
@@ -442,11 +448,17 @@ int git_futils_find_global_file(git_buf *path, const char *filename)
 	struct win32_path root;
 
 	if (win32_expand_path(&root, L"%USERPROFILE%\\") < 0 ||
-		win32_find_file(path, &root, filename) < 0) {
-		giterr_set(GITERR_OS, "Failed to lookup the current user's Windows profile");
+		root.path[0] == L'%') /* i.e. no expansion happened */
+	{
+		giterr_set(GITERR_OS, "Cannot locate the user's profile directory");
 		return -1;
 	}
 
+	if (win32_find_file(path, &root, filename) < 0) {
+		git_buf_clear(path);
+		return GIT_ENOTFOUND;
+	}
+
 	return 0;
 #else
 	const char *home = getenv("HOME");
diff --git a/tests-clar/core/env.c b/tests-clar/core/env.c
index fb483e89e..3bde85649 100644
--- a/tests-clar/core/env.c
+++ b/tests-clar/core/env.c
@@ -54,6 +54,7 @@ static int cl_setenv(const char *name, const char *value)
 
 #ifdef GIT_WIN32
 static char *env_userprofile = NULL;
+static char *env_programfiles = NULL;
 #else
 static char *env_home = NULL;
 #endif
@@ -62,6 +63,7 @@ void test_core_env__initialize(void)
 {
 #ifdef GIT_WIN32
 	env_userprofile = cl_getenv("USERPROFILE");
+	env_programfiles = cl_getenv("PROGRAMFILES");
 #else
 	env_home = cl_getenv("HOME");
 #endif
@@ -72,6 +74,8 @@ void test_core_env__cleanup(void)
 #ifdef GIT_WIN32
 	cl_setenv("USERPROFILE", env_userprofile);
 	git__free(env_userprofile);
+	cl_setenv("PROGRAMFILES", env_programfiles);
+	git__free(env_programfiles);
 #else
 	cl_setenv("HOME", env_home);
 #endif
@@ -128,3 +132,34 @@ void test_core_env__0(void)
 	git_buf_free(&path);
 	git_buf_free(&found);
 }
+
+void test_core_env__1(void)
+{
+	git_buf path = GIT_BUF_INIT;
+
+	cl_assert(git_futils_find_global_file(&path, "nonexistentfile") == GIT_ENOTFOUND);
+
+#ifdef GIT_WIN32
+	cl_git_pass(cl_setenv("USERPROFILE", "doesnotexist"));
+#else
+	cl_git_pass(cl_setenv("HOME", "doesnotexist"));
+#endif
+
+	cl_assert(git_futils_find_global_file(&path, "nonexistentfile") == GIT_ENOTFOUND);
+
+#ifdef GIT_WIN32
+	cl_git_pass(cl_setenv("USERPROFILE", NULL));
+#else
+	cl_git_pass(cl_setenv("HOME", NULL));
+#endif
+
+	cl_assert(git_futils_find_global_file(&path, "nonexistentfile") == -1);
+
+	cl_assert(git_futils_find_system_file(&path, "nonexistentfile") == GIT_ENOTFOUND);
+
+#ifdef GIT_WIN32
+	cl_git_pass(cl_setenv("PROGRAMFILES", NULL));
+
+	cl_assert(git_futils_find_system_file(&path, "nonexistentfile") == -1);
+#endif
+}