diff --git a/examples/status.c b/examples/status.c
index 2378c78b6..3c82640b2 100644
--- a/examples/status.c
+++ b/examples/status.c
@@ -203,7 +203,8 @@ int main(int argc, char *argv[])
 
 	opt.show  = GIT_STATUS_SHOW_INDEX_AND_WORKDIR;
 	opt.flags = GIT_STATUS_OPT_INCLUDE_UNTRACKED |
-		GIT_STATUS_OPT_RENAMES_HEAD_TO_INDEX;
+		GIT_STATUS_OPT_RENAMES_HEAD_TO_INDEX |
+		GIT_STATUS_OPT_SORT_CASE_SENSITIVELY;
 
 	for (i = 1; i < argc; ++i) {
 		if (argv[i][0] != '-') {
diff --git a/include/git2/status.h b/include/git2/status.h
index 282b606cb..63aea2f3b 100644
--- a/include/git2/status.h
+++ b/include/git2/status.h
@@ -111,6 +111,12 @@ typedef enum {
  * - GIT_STATUS_OPT_RENAMES_INDEX_TO_WORKDIR indicates tha rename
  *   detection should be run between the index and the working directory
  *   and enabled GIT_STATUS_WT_RENAMED as a possible status flag.
+ * - GIT_STATUS_OPT_SORT_CASE_SENSITIVELY overrides the native case
+ *   sensitivity for the file system and forces the output to be in
+ *   case-sensitive order
+ * - GIT_STATUS_OPT_SORT_CASE_INSENSITIVELY overrides the native case
+ *   sensitivity for the file system and forces the output to be in
+ *   case-insensitive order
  *
  * Calling `git_status_foreach()` is like calling the extended version
  * with: GIT_STATUS_OPT_INCLUDE_IGNORED, GIT_STATUS_OPT_INCLUDE_UNTRACKED,
@@ -127,6 +133,8 @@ typedef enum {
 	GIT_STATUS_OPT_RECURSE_IGNORED_DIRS     = (1u << 6),
 	GIT_STATUS_OPT_RENAMES_HEAD_TO_INDEX    = (1u << 7),
 	GIT_STATUS_OPT_RENAMES_INDEX_TO_WORKDIR = (1u << 8),
+	GIT_STATUS_OPT_SORT_CASE_SENSITIVELY    = (1u << 9),
+	GIT_STATUS_OPT_SORT_CASE_INSENSITIVELY  = (1u << 10),
 } git_status_opt_t;
 
 #define GIT_STATUS_OPT_DEFAULTS \
diff --git a/src/attr_file.c b/src/attr_file.c
index d059cfec7..d880398e8 100644
--- a/src/attr_file.c
+++ b/src/attr_file.c
@@ -498,7 +498,7 @@ int git_attr_assignment__parse(
 
 	assert(assigns && !assigns->length);
 
-	assigns->_cmp = sort_by_hash_and_name;
+	git_vector_set_cmp(assigns, sort_by_hash_and_name);
 
 	while (*scan && *scan != '\n') {
 		const char *name_start, *value_start;
diff --git a/src/diff.c b/src/diff.c
index 3846a5e1b..26e117402 100644
--- a/src/diff.c
+++ b/src/diff.c
@@ -365,7 +365,7 @@ static git_diff_list *diff_list_alloc(
 		diff->pfxcomp    = git__prefixcmp_icase;
 		diff->entrycomp  = git_index_entry__cmp_icase;
 
-		diff->deltas._cmp = git_diff_delta__casecmp;
+		git_vector_set_cmp(&diff->deltas, git_diff_delta__casecmp);
 	}
 
 	return diff;
@@ -1165,7 +1165,7 @@ int git_diff_tree_to_index(
 			d->pfxcomp    = git__prefixcmp_icase;
 			d->entrycomp  = git_index_entry__cmp_icase;
 
-			d->deltas._cmp = git_diff_delta__casecmp;
+			git_vector_set_cmp(&d->deltas, git_diff_delta__casecmp);
 			git_vector_sort(&d->deltas);
 		}
 	}
@@ -1266,10 +1266,10 @@ int git_diff__paired_foreach(
 	/* force case-sensitive delta sort */
 	if (icase_mismatch) {
 		if (head2idx->opts.flags & GIT_DIFF_DELTAS_ARE_ICASE) {
-			head2idx->deltas._cmp = git_diff_delta__cmp;
+			git_vector_set_cmp(&head2idx->deltas, git_diff_delta__cmp);
 			git_vector_sort(&head2idx->deltas);
 		} else {
-			idx2wd->deltas._cmp = git_diff_delta__cmp;
+			git_vector_set_cmp(&idx2wd->deltas, git_diff_delta__cmp);
 			git_vector_sort(&idx2wd->deltas);
 		}
 	}
@@ -1301,10 +1301,10 @@ int git_diff__paired_foreach(
 	/* restore case-insensitive delta sort */
 	if (icase_mismatch) {
 		if (head2idx->opts.flags & GIT_DIFF_DELTAS_ARE_ICASE) {
-			head2idx->deltas._cmp = git_diff_delta__casecmp;
+			git_vector_set_cmp(&head2idx->deltas, git_diff_delta__casecmp);
 			git_vector_sort(&head2idx->deltas);
 		} else {
-			idx2wd->deltas._cmp = git_diff_delta__casecmp;
+			git_vector_set_cmp(&idx2wd->deltas, git_diff_delta__casecmp);
 			git_vector_sort(&idx2wd->deltas);
 		}
 	}
diff --git a/src/index.c b/src/index.c
index d5568528b..1d46779bf 100644
--- a/src/index.c
+++ b/src/index.c
@@ -290,16 +290,16 @@ void git_index__set_ignore_case(git_index *index, bool ignore_case)
 {
 	index->ignore_case = ignore_case;
 
-	index->entries._cmp = ignore_case ? index_icmp : index_cmp;
 	index->entries_cmp_path = ignore_case ? index_icmp_path : index_cmp_path;
 	index->entries_search = ignore_case ? index_isrch : index_srch;
 	index->entries_search_path = ignore_case ? index_isrch_path : index_srch_path;
-	index->entries.sorted = 0;
+
+	git_vector_set_cmp(&index->entries, ignore_case ? index_icmp : index_cmp);
 	git_vector_sort(&index->entries);
 
-	index->reuc._cmp = ignore_case ? reuc_icmp : reuc_cmp;
 	index->reuc_search = ignore_case ? reuc_isrch : reuc_srch;
-	index->reuc.sorted = 0;
+
+	git_vector_set_cmp(&index->reuc, ignore_case ? reuc_icmp : reuc_cmp);
 	git_vector_sort(&index->reuc);
 }
 
@@ -2024,7 +2024,7 @@ int git_index_read_tree(git_index *index, const git_tree *tree)
 
 	git_vector_sort(&index->entries);
 
-	entries._cmp = index->entries._cmp;
+	git_vector_set_cmp(&entries, index->entries._cmp);
 	git_vector_swap(&entries, &index->entries);
 
 	git_index_clear(index);
diff --git a/src/status.c b/src/status.c
index 375100a89..e520c1017 100644
--- a/src/status.c
+++ b/src/status.c
@@ -335,8 +335,16 @@ int git_status_list_new(
 			status->head2idx, status->idx2wd, status_collect, status)) < 0)
 		goto done;
 
-	if ((flags & GIT_STATUS_OPT_RENAMES_HEAD_TO_INDEX) != 0 ||
-		(flags & GIT_STATUS_OPT_RENAMES_INDEX_TO_WORKDIR) != 0)
+	if (flags & GIT_STATUS_OPT_SORT_CASE_SENSITIVELY)
+		git_vector_set_cmp(&status->paired, status_entry_cmp);
+	if (flags & GIT_STATUS_OPT_SORT_CASE_INSENSITIVELY)
+		git_vector_set_cmp(&status->paired, status_entry_icmp);
+
+	if ((flags &
+		 (GIT_STATUS_OPT_RENAMES_HEAD_TO_INDEX |
+		  GIT_STATUS_OPT_RENAMES_INDEX_TO_WORKDIR |
+		  GIT_STATUS_OPT_SORT_CASE_SENSITIVELY |
+		  GIT_STATUS_OPT_SORT_CASE_INSENSITIVELY)) != 0)
 		git_vector_sort(&status->paired);
 
 done:
diff --git a/src/submodule.c b/src/submodule.c
index af488b7f3..89eba2aa4 100644
--- a/src/submodule.c
+++ b/src/submodule.c
@@ -151,7 +151,7 @@ int git_submodule_foreach(
 	int error;
 	git_submodule *sm;
 	git_vector seen = GIT_VECTOR_INIT;
-	seen._cmp = submodule_cmp;
+	git_vector_set_cmp(&seen, submodule_cmp);
 
 	assert(repo && callback);
 
diff --git a/src/vector.h b/src/vector.h
index e2f729b83..1bda9c93d 100644
--- a/src/vector.h
+++ b/src/vector.h
@@ -78,4 +78,13 @@ void git_vector_remove_matching(
 int git_vector_resize_to(git_vector *v, size_t new_length);
 int git_vector_set(void **old, git_vector *v, size_t position, void *value);
 
+/** Set the comparison function used for sorting the vector */
+GIT_INLINE(void) git_vector_set_cmp(git_vector *v, git_vector_cmp cmp)
+{
+	if (cmp != v->_cmp) {
+		v->_cmp = cmp;
+		v->sorted = 0;
+	}
+}
+
 #endif
diff --git a/tests-clar/status/status_helpers.c b/tests-clar/status/status_helpers.c
index f073c2491..902b65c4f 100644
--- a/tests-clar/status/status_helpers.c
+++ b/tests-clar/status/status_helpers.c
@@ -6,6 +6,9 @@ int cb_status__normal(
 {
 	status_entry_counts *counts = payload;
 
+	if (counts->debug)
+		cb_status__print(path, status_flags, NULL);
+
 	if (counts->entry_count >= counts->expected_entry_count) {
 		counts->wrong_status_flags_count++;
 		goto exit;
diff --git a/tests-clar/status/status_helpers.h b/tests-clar/status/status_helpers.h
index ae1469e79..f1f009e02 100644
--- a/tests-clar/status/status_helpers.h
+++ b/tests-clar/status/status_helpers.h
@@ -8,6 +8,7 @@ typedef struct {
 	const unsigned int* expected_statuses;
 	const char** expected_paths;
 	int expected_entry_count;
+	bool debug;
 } status_entry_counts;
 
 /* cb_status__normal takes payload of "status_entry_counts *" */
diff --git a/tests-clar/status/worktree.c b/tests-clar/status/worktree.c
index 7c27ee588..920671e13 100644
--- a/tests-clar/status/worktree.c
+++ b/tests-clar/status/worktree.c
@@ -743,3 +743,83 @@ void test_status_worktree__simple_delete_indexed(void)
 		GIT_STATUS_WT_DELETED, git_status_byindex(status, 0)->status);
 	git_status_list_free(status);
 }
+
+static const char *icase_paths[] = { "B", "c", "g", "H" };
+static unsigned int icase_statuses[] = {
+	GIT_STATUS_WT_MODIFIED, GIT_STATUS_WT_DELETED,
+	GIT_STATUS_WT_MODIFIED, GIT_STATUS_WT_DELETED,
+};
+
+static const char *case_paths[] = { "B", "H", "c", "g" };
+static unsigned int case_statuses[] = {
+	GIT_STATUS_WT_MODIFIED, GIT_STATUS_WT_DELETED,
+	GIT_STATUS_WT_DELETED, GIT_STATUS_WT_MODIFIED,
+};
+
+void test_status_worktree__sorting_by_case(void)
+{
+	git_repository *repo = cl_git_sandbox_init("icase");
+	git_index *index;
+	git_status_options opts = GIT_STATUS_OPTIONS_INIT;
+	bool native_ignore_case;
+	status_entry_counts counts;
+
+	cl_git_pass(git_repository_index(&index, repo));
+	native_ignore_case =
+		(git_index_caps(index) & GIT_INDEXCAP_IGNORE_CASE) != 0;
+	git_index_free(index);
+
+	memset(&counts, 0, sizeof(counts));
+	counts.expected_entry_count = 0;
+	counts.expected_paths = NULL;
+	counts.expected_statuses = NULL;
+	cl_git_pass(
+		git_status_foreach_ext(repo, &opts, cb_status__normal, &counts));
+	cl_assert_equal_i(counts.expected_entry_count, counts.entry_count);
+	cl_assert_equal_i(0, counts.wrong_status_flags_count);
+	cl_assert_equal_i(0, counts.wrong_sorted_path);
+
+	cl_git_rewritefile("icase/B", "new stuff");
+	cl_must_pass(p_unlink("icase/c"));
+	cl_git_rewritefile("icase/g", "new stuff");
+	cl_must_pass(p_unlink("icase/H"));
+
+	memset(&counts, 0, sizeof(counts));
+	counts.expected_entry_count = 4;
+	if (native_ignore_case) {
+		counts.expected_paths = icase_paths;
+		counts.expected_statuses = icase_statuses;
+	} else {
+		counts.expected_paths = case_paths;
+		counts.expected_statuses = case_statuses;
+	}
+	cl_git_pass(
+		git_status_foreach_ext(repo, &opts, cb_status__normal, &counts));
+	cl_assert_equal_i(counts.expected_entry_count, counts.entry_count);
+	cl_assert_equal_i(0, counts.wrong_status_flags_count);
+	cl_assert_equal_i(0, counts.wrong_sorted_path);
+
+	opts.flags = GIT_STATUS_OPT_SORT_CASE_SENSITIVELY;
+
+	memset(&counts, 0, sizeof(counts));
+	counts.expected_entry_count = 4;
+	counts.expected_paths = case_paths;
+	counts.expected_statuses = case_statuses;
+	cl_git_pass(
+		git_status_foreach_ext(repo, &opts, cb_status__normal, &counts));
+	cl_assert_equal_i(counts.expected_entry_count, counts.entry_count);
+	cl_assert_equal_i(0, counts.wrong_status_flags_count);
+	cl_assert_equal_i(0, counts.wrong_sorted_path);
+
+	opts.flags = GIT_STATUS_OPT_SORT_CASE_INSENSITIVELY;
+
+	memset(&counts, 0, sizeof(counts));
+	counts.expected_entry_count = 4;
+	counts.expected_paths = icase_paths;
+	counts.expected_statuses = icase_statuses;
+	cl_git_pass(
+		git_status_foreach_ext(repo, &opts, cb_status__normal, &counts));
+	cl_assert_equal_i(counts.expected_entry_count, counts.entry_count);
+	cl_assert_equal_i(0, counts.wrong_status_flags_count);
+	cl_assert_equal_i(0, counts.wrong_sorted_path);
+}