diff --git a/src/iterator.c b/src/iterator.c
index ce0fb0ec9..88b7ed28a 100644
--- a/src/iterator.c
+++ b/src/iterator.c
@@ -437,8 +437,10 @@ GIT_INLINE(bool) iterator_has_started(git_iterator *iter, const char *path)
 
 GIT_INLINE(bool) iterator_has_ended(git_iterator *iter, const char *path)
 {
-	if (iter->end == NULL || iter->ended == true)
+	if (iter->end == NULL)
 		return false;
+	else if (iter->ended)
+		return true;
 
 	iter->ended = (iter->prefixcomp(path, iter->end) > 0);
 	return iter->ended;
diff --git a/tests/repo/iterator.c b/tests/repo/iterator.c
index ea2b37d10..e668caf44 100644
--- a/tests/repo/iterator.c
+++ b/tests/repo/iterator.c
@@ -16,6 +16,17 @@ void test_repo_iterator__cleanup(void)
 	g_repo = NULL;
 }
 
+static void assert_at_end(git_iterator *i, bool verbose)
+{
+	const git_index_entry *end;
+	int error = git_iterator_advance(&end, i);
+
+	if (verbose && error != GIT_ITEROVER)
+		fprintf(stderr, "Expected end of iterator, got '%s'\n", end->path);
+
+	cl_git_fail_with(GIT_ITEROVER, error);
+}
+
 static void expect_iterator_items(
 	git_iterator *i,
 	int expected_flat,
@@ -57,6 +68,7 @@ static void expect_iterator_items(
 			break;
 	}
 
+	assert_at_end(i, v);
 	cl_assert_equal_i(expected_flat, count);
 
 	cl_git_pass(git_iterator_reset(i));
@@ -103,6 +115,7 @@ static void expect_iterator_items(
 			break;
 	}
 
+	assert_at_end(i, v);
 	cl_assert_equal_i(expected_total, count);
 }