diff --git a/tests/checkout/tree.c b/tests/checkout/tree.c
index 1d6552731..70905b843 100644
--- a/tests/checkout/tree.c
+++ b/tests/checkout/tree.c
@@ -1034,3 +1034,80 @@ void test_checkout_tree__removes_conflicts_only_by_pathscope(void)
 	git_commit_free(commit);
 	git_index_free(index);
 }
+
+void test_checkout_tree__case_changing_rename(void)
+{
+	git_index *index;
+	git_checkout_options opts = GIT_CHECKOUT_OPTIONS_INIT;
+	git_oid master_id, dir_commit_id, tree_id, commit_id;
+	git_commit *master_commit, *dir_commit;
+	git_tree *tree;
+	git_signature *signature;
+	const git_index_entry *index_entry;
+	bool case_sensitive;
+
+	assert_on_branch(g_repo, "master");
+
+	cl_git_pass(git_repository_index(&index, g_repo));
+
+	/* Switch branches and perform a case-changing rename */
+
+	opts.checkout_strategy = GIT_CHECKOUT_FORCE;
+
+	cl_git_pass(git_reference_name_to_id(&dir_commit_id, g_repo, "refs/heads/dir"));
+	cl_git_pass(git_commit_lookup(&dir_commit, g_repo, &dir_commit_id));
+
+	cl_git_pass(git_checkout_tree(g_repo, (git_object *)dir_commit, &opts));
+	cl_git_pass(git_repository_set_head(g_repo, "refs/heads/dir", NULL, NULL));
+
+	cl_assert(git_path_isfile("testrepo/README"));
+	case_sensitive = !git_path_isfile("testrepo/readme");
+
+	cl_assert(index_entry = git_index_get_bypath(index, "README", 0));
+	cl_assert_equal_s("README", index_entry->path);
+
+	cl_git_pass(git_index_remove_bypath(index, "README"));
+	cl_git_pass(p_rename("testrepo/README", "testrepo/__readme__"));
+	cl_git_pass(p_rename("testrepo/__readme__", "testrepo/readme"));
+	cl_git_append2file("testrepo/readme", "An addendum...");
+	cl_git_pass(git_index_add_bypath(index, "readme"));
+
+	cl_git_pass(git_index_write(index));
+
+	cl_git_pass(git_index_write_tree(&tree_id, index));
+	cl_git_pass(git_tree_lookup(&tree, g_repo, &tree_id));
+
+	cl_git_pass(git_signature_new(&signature, "Renamer", "rename@contoso.com", time(NULL), 0));
+
+	cl_git_pass(git_commit_create(&commit_id, g_repo, "refs/heads/dir", signature, signature, NULL, "case-changing rename", tree, 1, (const git_commit **)&dir_commit));
+
+	cl_assert(git_path_isfile("testrepo/readme"));
+	if (case_sensitive)
+		cl_assert(!git_path_isfile("testrepo/README"));
+
+	cl_assert(index_entry = git_index_get_bypath(index, "readme", 0));
+	cl_assert_equal_s("readme", index_entry->path);
+
+	/* Switching back to master should rename readme -> README */
+	opts.checkout_strategy = GIT_CHECKOUT_SAFE;
+
+	cl_git_pass(git_reference_name_to_id(&master_id, g_repo, "refs/heads/master"));
+	cl_git_pass(git_commit_lookup(&master_commit, g_repo, &master_id));
+
+	cl_git_pass(git_checkout_tree(g_repo, (git_object *)master_commit, &opts));
+	cl_git_pass(git_repository_set_head(g_repo, "refs/heads/master", NULL, NULL));
+	
+	assert_on_branch(g_repo, "master");
+
+	cl_assert(git_path_isfile("testrepo/README"));
+	if (case_sensitive)
+		cl_assert(!git_path_isfile("testrepo/readme"));
+
+	cl_assert(index_entry = git_index_get_bypath(index, "README", 0));
+	cl_assert_equal_s("README", index_entry->path);
+
+	git_signature_free(signature);
+	git_tree_free(tree);
+	git_commit_free(dir_commit);
+	git_commit_free(master_commit);
+}