diff --git a/tests-clar/checkout/checkout_helpers.c b/tests-clar/checkout/checkout_helpers.c
index 79e80c13a..ab93a89bd 100644
--- a/tests-clar/checkout/checkout_helpers.c
+++ b/tests-clar/checkout/checkout_helpers.c
@@ -50,35 +50,44 @@ void reset_index_to_treeish(git_object *treeish)
 	git_index_free(index);
 }
 
-static void test_file_contents_internal(
-	const char *path, const char *expectedcontents, bool strip_cr)
+static void check_file_contents_internal(
+	const char *path,
+	const char *expected_content,
+	bool strip_cr,
+	const char *file,
+	int line,
+	const char *msg)
 {
 	int fd;
 	char data[1024] = {0};
 	git_buf buf = GIT_BUF_INIT;
-	size_t expectedlen = strlen(expectedcontents);
+	size_t expected_len = expected_content ? strlen(expected_content) : 0;
 
 	fd = p_open(path, O_RDONLY);
 	cl_assert(fd >= 0);
 
 	buf.ptr = data;
-	buf.size = p_read(fd, buf.ptr, 1024);
+	buf.size = p_read(fd, buf.ptr, sizeof(data));
 
 	cl_git_pass(p_close(fd));
 
 	if (strip_cr)
 		strip_cr_from_buf(&buf);
 
-	cl_assert_equal_i((int)expectedlen, (int)buf.size);
-	cl_assert_equal_s(expectedcontents, buf.ptr);
+	clar__assert_equal_i((int)expected_len, (int)buf.size, file, line, "strlen(expected_content) != strlen(actual_content)", 1);
+	clar__assert_equal_s(expected_content, buf.ptr, file, line, msg, 1);
 }
 
-void test_file_contents(const char *path, const char *expected)
+void check_file_contents_at_line(
+	const char *path, const char *expected,
+	const char *file, int line, const char *msg)
 {
-	test_file_contents_internal(path, expected, false);
+	check_file_contents_internal(path, expected, false, file, line, msg);
 }
 
-void test_file_contents_nocr(const char *path, const char *expected)
+void check_file_contents_nocr_at_line(
+	const char *path, const char *expected,
+	const char *file, int line, const char *msg)
 {
-	test_file_contents_internal(path, expected, true);
+	check_file_contents_internal(path, expected, true, file, line, msg);
 }
diff --git a/tests-clar/checkout/checkout_helpers.h b/tests-clar/checkout/checkout_helpers.h
index 2c3a4b5bb..34053809d 100644
--- a/tests-clar/checkout/checkout_helpers.h
+++ b/tests-clar/checkout/checkout_helpers.h
@@ -5,5 +5,17 @@
 extern void strip_cr_from_buf(git_buf *buf);
 extern void assert_on_branch(git_repository *repo, const char *branch);
 extern void reset_index_to_treeish(git_object *treeish);
-extern void test_file_contents(const char *path, const char *expected);
-extern void test_file_contents_nocr(const char *path, const char *expected);
+
+extern void check_file_contents_at_line(
+	const char *path, const char *expected,
+	const char *file, int line, const char *msg);
+
+extern void check_file_contents_nocr_at_line(
+	const char *path, const char *expected,
+	const char *file, int line, const char *msg);
+
+#define check_file_contents(PATH,EXP) \
+	check_file_contents_at_line(PATH,EXP,__FILE__,__LINE__,"String mismatch: " #EXP " != " #PATH)
+
+#define check_file_contents_nocr(PATH,EXP) \
+	check_file_contents_nocr_at_line(PATH,EXP,__FILE__,__LINE__,"String mismatch: " #EXP " != " #PATH)
diff --git a/tests-clar/checkout/crlf.c b/tests-clar/checkout/crlf.c
index 40f083c1c..285b1f272 100644
--- a/tests-clar/checkout/crlf.c
+++ b/tests-clar/checkout/crlf.c
@@ -28,7 +28,6 @@ void test_checkout_crlf__cleanup(void)
 
 void test_checkout_crlf__detect_crlf_autocrlf_false(void)
 {
-#ifdef GIT_WIN32
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
 	opts.checkout_strategy = GIT_CHECKOUT_SAFE_CREATE;
 
@@ -36,14 +35,12 @@ void test_checkout_crlf__detect_crlf_autocrlf_false(void)
 
 	git_checkout_head(g_repo, &opts);
 
-	test_file_contents("./crlf/all-lf", ALL_LF_TEXT_RAW);
-	test_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
-#endif
+	check_file_contents("./crlf/all-lf", ALL_LF_TEXT_RAW);
+	check_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
 }
 
 void test_checkout_crlf__autocrlf_false_index_size_is_unfiltered_size(void)
 {
-#ifdef GIT_WIN32
 	git_index *index;
 	const git_index_entry *entry;
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
@@ -62,12 +59,10 @@ void test_checkout_crlf__autocrlf_false_index_size_is_unfiltered_size(void)
 	cl_assert(entry->file_size == strlen(ALL_CRLF_TEXT_RAW));
 
 	git_index_free(index);
-#endif
 }
 
 void test_checkout_crlf__detect_crlf_autocrlf_true(void)
 {
-#ifdef GIT_WIN32
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
 	opts.checkout_strategy = GIT_CHECKOUT_SAFE_CREATE;
 
@@ -75,14 +70,16 @@ void test_checkout_crlf__detect_crlf_autocrlf_true(void)
 
 	git_checkout_head(g_repo, &opts);
 
-	test_file_contents("./crlf/all-lf", ALL_LF_TEXT_AS_CRLF);
-	test_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
-#endif
+	if (GIT_EOL_NATIVE == GIT_EOL_LF)
+		check_file_contents("./crlf/all-lf", ALL_LF_TEXT_RAW);
+	else
+		check_file_contents("./crlf/all-lf", ALL_LF_TEXT_AS_CRLF);
+
+	check_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
 }
 
 void test_checkout_crlf__more_lf_autocrlf_true(void)
 {
-#ifdef GIT_WIN32
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
 	opts.checkout_strategy = GIT_CHECKOUT_SAFE_CREATE;
 
@@ -90,13 +87,14 @@ void test_checkout_crlf__more_lf_autocrlf_true(void)
 
 	git_checkout_head(g_repo, &opts);
 
-	test_file_contents("./crlf/more-lf", MORE_LF_TEXT_AS_CRLF);
-#endif
+	if (GIT_EOL_NATIVE == GIT_EOL_LF)
+		check_file_contents("./crlf/more-lf", MORE_LF_TEXT_RAW);
+	else
+		check_file_contents("./crlf/more-lf", MORE_LF_TEXT_AS_CRLF);
 }
 
 void test_checkout_crlf__more_crlf_autocrlf_true(void)
 {
-#ifdef GIT_WIN32
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
 	opts.checkout_strategy = GIT_CHECKOUT_SAFE_CREATE;
 
@@ -104,13 +102,14 @@ void test_checkout_crlf__more_crlf_autocrlf_true(void)
 
 	git_checkout_head(g_repo, &opts);
 
-	test_file_contents("./crlf/more-crlf", MORE_CRLF_TEXT_AS_CRLF);
-#endif
+	if (GIT_EOL_NATIVE == GIT_EOL_LF)
+		check_file_contents("./crlf/more-crlf", MORE_CRLF_TEXT_RAW);
+	else
+		check_file_contents("./crlf/more-crlf", MORE_CRLF_TEXT_AS_CRLF);
 }
 
 void test_checkout_crlf__all_crlf_autocrlf_true(void)
 {
-#ifdef GIT_WIN32
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
 	opts.checkout_strategy = GIT_CHECKOUT_SAFE_CREATE;
 
@@ -118,13 +117,11 @@ void test_checkout_crlf__all_crlf_autocrlf_true(void)
 
 	git_checkout_head(g_repo, &opts);
 
-	test_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
-#endif
+	check_file_contents("./crlf/all-crlf", ALL_CRLF_TEXT_RAW);
 }
 
 void test_checkout_crlf__autocrlf_true_index_size_is_filtered_size(void)
 {
-#ifdef GIT_WIN32
 	git_index *index;
 	const git_index_entry *entry;
 	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
@@ -137,11 +134,14 @@ void test_checkout_crlf__autocrlf_true_index_size_is_filtered_size(void)
 	git_repository_index(&index, g_repo);
 
 	cl_assert((entry = git_index_get_bypath(index, "all-lf", 0)) != NULL);
-	cl_assert(entry->file_size == strlen(ALL_LF_TEXT_AS_CRLF));
+
+	if (GIT_EOL_NATIVE == GIT_EOL_LF)
+		cl_assert_equal_sz(strlen(ALL_LF_TEXT_RAW), entry->file_size);
+	else
+		cl_assert_equal_sz(strlen(ALL_LF_TEXT_AS_CRLF), entry->file_size);
 
 	cl_assert((entry = git_index_get_bypath(index, "all-crlf", 0)) != NULL);
-	cl_assert(entry->file_size == strlen(ALL_CRLF_TEXT_RAW));
+	cl_assert_equal_sz(strlen(ALL_CRLF_TEXT_RAW), entry->file_size);
 
 	git_index_free(index);
-#endif
 }
diff --git a/tests-clar/checkout/index.c b/tests-clar/checkout/index.c
index 33506a669..78ff5ac62 100644
--- a/tests-clar/checkout/index.c
+++ b/tests-clar/checkout/index.c
@@ -48,9 +48,9 @@ void test_checkout_index__can_create_missing_files(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/README", "hey there\n");
-	test_file_contents("./testrepo/branch_file.txt", "hi\nbye!\n");
-	test_file_contents("./testrepo/new.txt", "my new file\n");
+	check_file_contents("./testrepo/README", "hey there\n");
+	check_file_contents("./testrepo/branch_file.txt", "hi\nbye!\n");
+	check_file_contents("./testrepo/new.txt", "my new file\n");
 }
 
 void test_checkout_index__can_remove_untracked_files(void)
@@ -88,8 +88,8 @@ void test_checkout_index__honor_the_specified_pathspecs(void)
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
 	cl_assert_equal_i(false, git_path_isfile("./testrepo/README"));
-	test_file_contents("./testrepo/branch_file.txt", "hi\nbye!\n");
-	test_file_contents("./testrepo/new.txt", "my new file\n");
+	check_file_contents("./testrepo/branch_file.txt", "hi\nbye!\n");
+	check_file_contents("./testrepo/new.txt", "my new file\n");
 }
 
 void test_checkout_index__honor_the_gitattributes_directives(void)
@@ -106,9 +106,9 @@ void test_checkout_index__honor_the_gitattributes_directives(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/README", "hey there\n");
-	test_file_contents("./testrepo/new.txt", "my new file\n");
-	test_file_contents("./testrepo/branch_file.txt", "hi\r\nbye!\r\n");
+	check_file_contents("./testrepo/README", "hey there\n");
+	check_file_contents("./testrepo/new.txt", "my new file\n");
+	check_file_contents("./testrepo/branch_file.txt", "hi\r\nbye!\r\n");
 }
 
 void test_checkout_index__honor_coreautocrlf_setting_set_to_true(void)
@@ -124,7 +124,7 @@ void test_checkout_index__honor_coreautocrlf_setting_set_to_true(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/README", expected_readme_text);
+	check_file_contents("./testrepo/README", expected_readme_text);
 #endif
 }
 
@@ -139,7 +139,7 @@ void test_checkout_index__honor_coresymlinks_setting_set_to_true(void)
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
 #ifdef GIT_WIN32
-	test_file_contents("./testrepo/link_to_new.txt", "new.txt");
+	check_file_contents("./testrepo/link_to_new.txt", "new.txt");
 #else
 	{
 		char link_data[1024];
@@ -149,7 +149,7 @@ void test_checkout_index__honor_coresymlinks_setting_set_to_true(void)
 		link_data[link_size] = '\0';
 		cl_assert_equal_i(link_size, strlen("new.txt"));
 		cl_assert_equal_s(link_data, "new.txt");
-		test_file_contents("./testrepo/link_to_new.txt", "my new file\n");
+		check_file_contents("./testrepo/link_to_new.txt", "my new file\n");
 	}
 #endif
 }
@@ -164,7 +164,7 @@ void test_checkout_index__honor_coresymlinks_setting_set_to_false(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/link_to_new.txt", "new.txt");
+	check_file_contents("./testrepo/link_to_new.txt", "new.txt");
 }
 
 void test_checkout_index__donot_overwrite_modified_file_by_default(void)
@@ -180,7 +180,7 @@ void test_checkout_index__donot_overwrite_modified_file_by_default(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/new.txt", "This isn't what's stored!");
+	check_file_contents("./testrepo/new.txt", "This isn't what's stored!");
 }
 
 void test_checkout_index__can_overwrite_modified_file(void)
@@ -193,7 +193,7 @@ void test_checkout_index__can_overwrite_modified_file(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/new.txt", "my new file\n");
+	check_file_contents("./testrepo/new.txt", "my new file\n");
 }
 
 void test_checkout_index__options_disable_filters(void)
@@ -207,14 +207,14 @@ void test_checkout_index__options_disable_filters(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/new.txt", "my new file\r\n");
+	check_file_contents("./testrepo/new.txt", "my new file\r\n");
 
 	p_unlink("./testrepo/new.txt");
 
 	opts.disable_filters = true;
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/new.txt", "my new file\n");
+	check_file_contents("./testrepo/new.txt", "my new file\n");
 }
 
 void test_checkout_index__options_dir_modes(void)
@@ -274,7 +274,7 @@ void test_checkout_index__options_open_flags(void)
 	opts.checkout_strategy = GIT_CHECKOUT_FORCE;
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./testrepo/new.txt", "hi\nmy new file\n");
+	check_file_contents("./testrepo/new.txt", "hi\nmy new file\n");
 }
 
 struct notify_data {
@@ -469,9 +469,9 @@ void test_checkout_index__can_update_prefixed_files(void)
 	/* remove untracked will remove the .gitattributes file before the blobs
 	 * were created, so they will have had crlf filtering applied on Windows
 	 */
-	test_file_contents_nocr("./testrepo/README", "hey there\n");
-	test_file_contents_nocr("./testrepo/branch_file.txt", "hi\nbye!\n");
-	test_file_contents_nocr("./testrepo/new.txt", "my new file\n");
+	check_file_contents_nocr("./testrepo/README", "hey there\n");
+	check_file_contents_nocr("./testrepo/branch_file.txt", "hi\nbye!\n");
+	check_file_contents_nocr("./testrepo/new.txt", "my new file\n");
 
 	cl_assert(!git_path_exists("testrepo/READ"));
 	cl_assert(!git_path_exists("testrepo/README.after"));
@@ -503,5 +503,5 @@ void test_checkout_index__issue_1397(void)
 
 	cl_git_pass(git_checkout_index(g_repo, NULL, &opts));
 
-	test_file_contents("./issue_1397/crlf_file.txt", "first line\r\nsecond line\r\nboth with crlf");
+	check_file_contents("./issue_1397/crlf_file.txt", "first line\r\nsecond line\r\nboth with crlf");
 }
diff --git a/tests-clar/checkout/tree.c b/tests-clar/checkout/tree.c
index 2a8fbc457..5a2eacea1 100644
--- a/tests-clar/checkout/tree.c
+++ b/tests-clar/checkout/tree.c
@@ -248,7 +248,7 @@ void test_checkout_tree__can_update_only(void)
 
 	cl_assert(!git_path_isdir("testrepo/a"));
 
-	test_file_contents_nocr("testrepo/branch_file.txt", "hi\nbye!\n");
+	check_file_contents_nocr("testrepo/branch_file.txt", "hi\nbye!\n");
 
 	/* now checkout branch but with update only */
 
@@ -269,7 +269,7 @@ void test_checkout_tree__can_update_only(void)
 	cl_assert(!git_path_isdir("testrepo/a"));
 
 	/* but this file still should have been updated */
-	test_file_contents_nocr("testrepo/branch_file.txt", "hi\n");
+	check_file_contents_nocr("testrepo/branch_file.txt", "hi\n");
 
 	git_object_free(obj);
 }
@@ -500,7 +500,7 @@ void test_checkout_tree__issue_1397(void)
 
 	cl_git_pass(git_checkout_tree(g_repo, tree, &opts));
 
-	test_file_contents("./issue_1397/crlf_file.txt", "first line\r\nsecond line\r\nboth with crlf");
+	check_file_contents("./issue_1397/crlf_file.txt", "first line\r\nsecond line\r\nboth with crlf");
 
 	git_object_free(tree);
 }