diff --git a/src/config_file.c b/src/config_file.c
index 7106f18db..8f55c42f3 100644
--- a/src/config_file.c
+++ b/src/config_file.c
@@ -1163,7 +1163,7 @@ static int strip_comments(char *line, int in_quotes)
 	}
 
 	/* skip any space at the end */
-	if (ptr > line && git__isspace(ptr[-1])) {
+	while (ptr > line && git__isspace(ptr[-1])) {
 		ptr--;
 	}
 	ptr[0] = '\0';
diff --git a/tests/config/stress.c b/tests/config/stress.c
index 488915e79..e8e9d2b61 100644
--- a/tests/config/stress.c
+++ b/tests/config/stress.c
@@ -44,12 +44,24 @@ void test_config_stress__comments(void)
 
 	cl_git_pass(git_config_open_ondisk(&config, cl_fixture("config/config12")));
 
+	cl_git_pass(git_config_get_string(&str, config, "some.section.test2"));
+	cl_assert_equal_s("hello", str);
+
+	cl_git_pass(git_config_get_string(&str, config, "some.section.test3"));
+	cl_assert_equal_s("welcome", str);
+
 	cl_git_pass(git_config_get_string(&str, config, "some.section.other"));
 	cl_assert_equal_s("hello! \" ; ; ; ", str);
 
+	cl_git_pass(git_config_get_string(&str, config, "some.section.other2"));
+	cl_assert_equal_s("cool! \" # # # ", str);
+
 	cl_git_pass(git_config_get_string(&str, config, "some.section.multi"));
 	cl_assert_equal_s("hi, this is a ; multiline comment # with ;\n special chars and other stuff !@#", str);
 
+	cl_git_pass(git_config_get_string(&str, config, "some.section.multi2"));
+	cl_assert_equal_s("good, this is a ; multiline comment # with ;\n special chars and other stuff !@#", str);
+
 	cl_git_pass(git_config_get_string(&str, config, "some.section.back"));
 	cl_assert_equal_s("this is \ba phrase", str);
 
diff --git a/tests/resources/config/config12 b/tests/resources/config/config12
index b57a81b08..6917880b5 100644
Binary files a/tests/resources/config/config12 and b/tests/resources/config/config12 differ