diff --git a/src/attr.c b/src/attr.c
index 622874348..6b9a3d614 100644
--- a/src/attr.c
+++ b/src/attr.c
@@ -217,6 +217,74 @@ cleanup:
 	return error;
 }
 
+static int preload_attr_file(
+	git_repository *repo,
+	git_attr_file_source source,
+	const char *base,
+	const char *file)
+{
+	int error;
+	git_attr_file *preload = NULL;
+
+	if (!file)
+		return 0;
+	if (!(error = git_attr_cache__get(
+			&preload, repo, source, base, file, git_attr_file__parse_buffer)))
+		git_attr_file__free(preload);
+
+	return error;
+}
+
+static int attr_setup(git_repository *repo)
+{
+	int error = 0;
+	const char *workdir = git_repository_workdir(repo);
+	git_index *idx = NULL;
+	git_buf sys = GIT_BUF_INIT;
+
+	if ((error = git_attr_cache__init(repo)) < 0)
+		return error;
+
+	/* preload attribute files that could contain macros so the
+	 * definitions will be available for later file parsing
+	 */
+
+	if (!(error = git_sysdir_find_system_file(&sys, GIT_ATTR_FILE_SYSTEM))) {
+		error = preload_attr_file(
+			repo, GIT_ATTR_FILE__FROM_FILE, NULL, sys.ptr);
+		git_buf_free(&sys);
+	}
+	if (error < 0) {
+		if (error == GIT_ENOTFOUND) {
+			giterr_clear();
+			error = 0;
+		} else
+			return error;
+	}
+
+	if ((error = preload_attr_file(
+			repo, GIT_ATTR_FILE__FROM_FILE,
+			NULL, git_repository_attr_cache(repo)->cfg_attr_file)) < 0)
+		return error;
+
+	if ((error = preload_attr_file(
+			repo, GIT_ATTR_FILE__FROM_FILE,
+			git_repository_path(repo), GIT_ATTR_FILE_INREPO)) < 0)
+		return error;
+
+	if (workdir != NULL &&
+		(error = preload_attr_file(
+			repo, GIT_ATTR_FILE__FROM_FILE, workdir, GIT_ATTR_FILE)) < 0)
+		return error;
+
+	if ((error = git_repository_index__weakptr(&idx, repo)) < 0 ||
+		(error = preload_attr_file(
+			repo, GIT_ATTR_FILE__FROM_INDEX, NULL, GIT_ATTR_FILE)) < 0)
+		return error;
+
+	return error;
+}
+
 int git_attr_add_macro(
 	git_repository *repo,
 	const char *name,
@@ -226,8 +294,8 @@ int git_attr_add_macro(
 	git_attr_rule *macro = NULL;
 	git_pool *pool;
 
-	if (git_attr_cache__init(repo) < 0)
-		return -1;
+	if ((error = attr_setup(repo)) < 0)
+		return error;
 
 	macro = git__calloc(1, sizeof(git_attr_rule));
 	GITERR_CHECK_ALLOC(macro);
@@ -348,7 +416,7 @@ static int collect_attr_files(
 	const char *workdir = git_repository_workdir(repo);
 	attr_walk_up_info info = { NULL };
 
-	if ((error = git_attr_cache__init(repo)) < 0)
+	if ((error = attr_setup(repo)) < 0)
 		return error;
 
 	/* Resolve path in a non-bare repo */
diff --git a/src/attr_file.c b/src/attr_file.c
index 65bbf78e8..8a8d86a2d 100644
--- a/src/attr_file.c
+++ b/src/attr_file.c
@@ -248,9 +248,7 @@ int git_attr_file__parse_buffer(
 				repo, &attrs->pool, &rule->assigns, &scan)))
 		{
 			if (rule->match.flags & GIT_ATTR_FNMATCH_MACRO)
-				/* should generate error/warning if this is coming from any
-				 * file other than .gitattributes at repo root.
-				 */
+				/* TODO: warning if macro found in file below repo root */
 				error = git_attr_cache__insert_macro(repo, rule);
 			else
 				error = git_vector_insert(&attrs->rules, rule);
diff --git a/tests/attr/repo.c b/tests/attr/repo.c
index 71dc7a5b5..9aab7ed96 100644
--- a/tests/attr/repo.c
+++ b/tests/attr/repo.c
@@ -23,49 +23,74 @@ void test_attr_repo__cleanup(void)
 	g_repo = NULL;
 }
 
+static struct attr_expected get_one_test_cases[] = {
+	{ "root_test1", "repoattr", EXPECT_TRUE, NULL },
+	{ "root_test1", "rootattr", EXPECT_TRUE, NULL },
+	{ "root_test1", "missingattr", EXPECT_UNDEFINED, NULL },
+	{ "root_test1", "subattr", EXPECT_UNDEFINED, NULL },
+	{ "root_test1", "negattr", EXPECT_UNDEFINED, NULL },
+	{ "root_test2", "repoattr", EXPECT_TRUE, NULL },
+	{ "root_test2", "rootattr", EXPECT_FALSE, NULL },
+	{ "root_test2", "missingattr", EXPECT_UNDEFINED, NULL },
+	{ "root_test2", "multiattr", EXPECT_FALSE, NULL },
+	{ "root_test3", "repoattr", EXPECT_TRUE, NULL },
+	{ "root_test3", "rootattr", EXPECT_UNDEFINED, NULL },
+	{ "root_test3", "multiattr", EXPECT_STRING, "3" },
+	{ "root_test3", "multi2", EXPECT_UNDEFINED, NULL },
+	{ "sub/subdir_test1", "repoattr", EXPECT_TRUE, NULL },
+	{ "sub/subdir_test1", "rootattr", EXPECT_TRUE, NULL },
+	{ "sub/subdir_test1", "missingattr", EXPECT_UNDEFINED, NULL },
+	{ "sub/subdir_test1", "subattr", EXPECT_STRING, "yes" },
+	{ "sub/subdir_test1", "negattr", EXPECT_FALSE, NULL },
+	{ "sub/subdir_test1", "another", EXPECT_UNDEFINED, NULL },
+	{ "sub/subdir_test2.txt", "repoattr", EXPECT_TRUE, NULL },
+	{ "sub/subdir_test2.txt", "rootattr", EXPECT_TRUE, NULL },
+	{ "sub/subdir_test2.txt", "missingattr", EXPECT_UNDEFINED, NULL },
+	{ "sub/subdir_test2.txt", "subattr", EXPECT_STRING, "yes" },
+	{ "sub/subdir_test2.txt", "negattr", EXPECT_FALSE, NULL },
+	{ "sub/subdir_test2.txt", "another", EXPECT_STRING, "zero" },
+	{ "sub/subdir_test2.txt", "reposub", EXPECT_TRUE, NULL },
+	{ "sub/sub/subdir.txt", "another", EXPECT_STRING, "one" },
+	{ "sub/sub/subdir.txt", "reposubsub", EXPECT_TRUE, NULL },
+	{ "sub/sub/subdir.txt", "reposub", EXPECT_UNDEFINED, NULL },
+	{ "does-not-exist", "foo", EXPECT_STRING, "yes" },
+	{ "sub/deep/file", "deepdeep", EXPECT_TRUE, NULL },
+	{ "sub/sub/d/no", "test", EXPECT_STRING, "a/b/d/*" },
+	{ "sub/sub/d/yes", "test", EXPECT_UNDEFINED, NULL },
+};
+
 void test_attr_repo__get_one(void)
 {
-	struct attr_expected test_cases[] = {
-		{ "root_test1", "repoattr", EXPECT_TRUE, NULL },
-		{ "root_test1", "rootattr", EXPECT_TRUE, NULL },
-		{ "root_test1", "missingattr", EXPECT_UNDEFINED, NULL },
-		{ "root_test1", "subattr", EXPECT_UNDEFINED, NULL },
-		{ "root_test1", "negattr", EXPECT_UNDEFINED, NULL },
-		{ "root_test2", "repoattr", EXPECT_TRUE, NULL },
-		{ "root_test2", "rootattr", EXPECT_FALSE, NULL },
-		{ "root_test2", "missingattr", EXPECT_UNDEFINED, NULL },
-		{ "root_test2", "multiattr", EXPECT_FALSE, NULL },
-		{ "root_test3", "repoattr", EXPECT_TRUE, NULL },
-		{ "root_test3", "rootattr", EXPECT_UNDEFINED, NULL },
-		{ "root_test3", "multiattr", EXPECT_STRING, "3" },
-		{ "root_test3", "multi2", EXPECT_UNDEFINED, NULL },
-		{ "sub/subdir_test1", "repoattr", EXPECT_TRUE, NULL },
-		{ "sub/subdir_test1", "rootattr", EXPECT_TRUE, NULL },
-		{ "sub/subdir_test1", "missingattr", EXPECT_UNDEFINED, NULL },
-		{ "sub/subdir_test1", "subattr", EXPECT_STRING, "yes" },
-		{ "sub/subdir_test1", "negattr", EXPECT_FALSE, NULL },
-		{ "sub/subdir_test1", "another", EXPECT_UNDEFINED, NULL },
-		{ "sub/subdir_test2.txt", "repoattr", EXPECT_TRUE, NULL },
-		{ "sub/subdir_test2.txt", "rootattr", EXPECT_TRUE, NULL },
-		{ "sub/subdir_test2.txt", "missingattr", EXPECT_UNDEFINED, NULL },
-		{ "sub/subdir_test2.txt", "subattr", EXPECT_STRING, "yes" },
-		{ "sub/subdir_test2.txt", "negattr", EXPECT_FALSE, NULL },
-		{ "sub/subdir_test2.txt", "another", EXPECT_STRING, "zero" },
-		{ "sub/subdir_test2.txt", "reposub", EXPECT_TRUE, NULL },
-		{ "sub/sub/subdir.txt", "another", EXPECT_STRING, "one" },
-		{ "sub/sub/subdir.txt", "reposubsub", EXPECT_TRUE, NULL },
-		{ "sub/sub/subdir.txt", "reposub", EXPECT_UNDEFINED, NULL },
-		{ "does-not-exist", "foo", EXPECT_STRING, "yes" },
-		{ "sub/deep/file", "deepdeep", EXPECT_TRUE, NULL },
-		{ "sub/sub/d/no", "test", EXPECT_STRING, "a/b/d/*" },
-		{ "sub/sub/d/yes", "test", EXPECT_UNDEFINED, NULL },
-		{ NULL, NULL, 0, NULL }
-	}, *scan;
+	int i;
 
-	for (scan = test_cases; scan->path != NULL; scan++) {
+	for (i = 0; i < (int)ARRAY_SIZE(get_one_test_cases); ++i) {
+		struct attr_expected *scan = &get_one_test_cases[i];
 		const char *value;
+
 		cl_git_pass(git_attr_get(&value, g_repo, 0, scan->path, scan->attr));
-		attr_check_expected(scan->expected, scan->expected_str, scan->attr, value);
+		attr_check_expected(
+			scan->expected, scan->expected_str, scan->attr, value);
+	}
+
+	cl_assert(git_attr_cache__is_cached(
+		g_repo, GIT_ATTR_FILE__FROM_FILE, ".git/info/attributes"));
+	cl_assert(git_attr_cache__is_cached(
+		g_repo, GIT_ATTR_FILE__FROM_FILE, ".gitattributes"));
+	cl_assert(git_attr_cache__is_cached(
+		g_repo, GIT_ATTR_FILE__FROM_FILE, "sub/.gitattributes"));
+}
+
+void test_attr_repo__get_one_start_deep(void)
+{
+	int i;
+
+	for (i = (int)ARRAY_SIZE(get_one_test_cases) - 1; i >= 0; --i) {
+		struct attr_expected *scan = &get_one_test_cases[i];
+		const char *value;
+
+		cl_git_pass(git_attr_get(&value, g_repo, 0, scan->path, scan->attr));
+		attr_check_expected(
+			scan->expected, scan->expected_str, scan->attr, value);
 	}
 
 	cl_assert(git_attr_cache__is_cached(