diff --git a/src/attr_file.c b/src/attr_file.c
index 3e95a2134..07ffacbaf 100644
--- a/src/attr_file.c
+++ b/src/attr_file.c
@@ -378,6 +378,18 @@ bool git_attr_fnmatch__match(
 		return (matchval != FNM_NOMATCH);
 	}
 
+	/* if path is a directory prefix of a negated pattern, then match */
+	if ((match->flags & GIT_ATTR_FNMATCH_NEGATIVE) && path->is_dir) {
+		size_t pathlen = strlen(path->path);
+		bool prefixed = (pathlen <= match->length) &&
+			((match->flags & GIT_ATTR_FNMATCH_ICASE) ?
+			 !strncasecmp(match->pattern, path->path, pathlen) :
+			 !strncmp(match->pattern, path->path, pathlen));
+
+		if (prefixed && git_path_at_end_of_segment(&match->pattern[pathlen]))
+			return true;
+	}
+
 	return (p_fnmatch(match->pattern, filename, flags) != FNM_NOMATCH);
 }
 
@@ -522,7 +534,8 @@ int git_attr_fnmatch__parse(
 	}
 
 	if (*pattern == '!' && (spec->flags & GIT_ATTR_FNMATCH_ALLOWNEG) != 0) {
-		spec->flags = spec->flags | GIT_ATTR_FNMATCH_NEGATIVE;
+		spec->flags = spec->flags |
+			GIT_ATTR_FNMATCH_NEGATIVE | GIT_ATTR_FNMATCH_LEADINGDIR;
 		pattern++;
 	}
 
diff --git a/src/path.h b/src/path.h
index 2e86241e1..46d6efe93 100644
--- a/src/path.h
+++ b/src/path.h
@@ -128,6 +128,14 @@ GIT_INLINE(int) git_path_is_relative(const char *p)
 	return (p[0] == '.' && (p[1] == '/' || (p[1] == '.' && p[2] == '/')));
 }
 
+/**
+ * Check if string is at end of path segment (i.e. looking at '/' or '\0')
+ */
+GIT_INLINE(int) git_path_at_end_of_segment(const char *p)
+{
+	return !*p || *p == '/';
+}
+
 extern int git__percent_decode(git_buf *decoded_out, const char *input);
 
 /**
diff --git a/tests/status/ignore.c b/tests/status/ignore.c
index a4e766fdf..b2af79074 100644
--- a/tests/status/ignore.c
+++ b/tests/status/ignore.c
@@ -788,3 +788,98 @@ void test_status_ignore__negative_ignores_inside_ignores(void)
 	refute_is_ignored("top/mid/btm/tracked");
 	refute_is_ignored("top/mid/btm/untracked");
 }
+
+void test_status_ignore__negative_ignores_in_slash_star(void)
+{
+	git_status_options status_opts = GIT_STATUS_OPTIONS_INIT;
+	git_status_list *list;
+	int found_look_ma = 0, found_what_about = 0;
+	size_t i;
+	static const char *test_files[] = {
+		"empty_standard_repo/bin/look-ma.txt",
+		"empty_standard_repo/bin/what-about-me.txt",
+		NULL
+	};
+
+	make_test_data("empty_standard_repo", test_files);
+	cl_git_mkfile(
+		"empty_standard_repo/.gitignore",
+		"bin/*\n"
+		"!bin/w*\n");
+
+	assert_is_ignored("bin/look-ma.txt");
+	refute_is_ignored("bin/what-about-me.txt");
+
+	status_opts.flags = GIT_STATUS_OPT_DEFAULTS;
+	cl_git_pass(git_status_list_new(&list, g_repo, &status_opts));
+	for (i = 0; i < git_status_list_entrycount(list); i++) {
+		const git_status_entry *entry = git_status_byindex(list, i);
+
+		if (!strcmp("bin/look-ma.txt", entry->index_to_workdir->new_file.path))
+			found_look_ma = 1;
+
+		if (!strcmp("bin/what-about-me.txt", entry->index_to_workdir->new_file.path))
+			found_what_about = 1;
+	}
+	git_status_list_free(list);
+
+	cl_assert(found_look_ma);
+	cl_assert(found_what_about);
+}
+
+void test_status_ignore__negative_ignores_without_trailing_slash_inside_ignores(void)
+{
+	git_status_options status_opts = GIT_STATUS_OPTIONS_INIT;
+	git_status_list *list;
+	int found_parent_file = 0, found_parent_child1_file = 0, found_parent_child2_file = 0;
+	size_t i;
+	static const char *test_files[] = {
+		"empty_standard_repo/parent/file.txt",
+		"empty_standard_repo/parent/force.txt",
+		"empty_standard_repo/parent/child1/file.txt",
+		"empty_standard_repo/parent/child2/file.txt",
+		NULL
+	};
+
+	make_test_data("empty_standard_repo", test_files);
+	cl_git_mkfile(
+		"empty_standard_repo/.gitignore",
+		"parent/*\n"
+		"!parent/force.txt\n"
+		"!parent/child1\n"
+		"!parent/child2/\n");
+
+	add_one_to_index("parent/force.txt");
+
+	assert_is_ignored("parent/file.txt");
+	refute_is_ignored("parent/force.txt");
+	refute_is_ignored("parent/child1/file.txt");
+	refute_is_ignored("parent/child2/file.txt");
+
+	status_opts.flags = GIT_STATUS_OPT_DEFAULTS;
+	cl_git_pass(git_status_list_new(&list, g_repo, &status_opts));
+	for (i = 0; i < git_status_list_entrycount(list); i++) {
+		const git_status_entry *entry = git_status_byindex(list, i);
+
+		if (!entry->index_to_workdir)
+			continue;
+
+		if (!strcmp("parent/file.txt", entry->index_to_workdir->new_file.path))
+			found_parent_file = 1;
+
+		if (!strcmp("parent/force.txt", entry->index_to_workdir->new_file.path))
+			found_parent_file = 1;
+
+		if (!strcmp("parent/child1/file.txt", entry->index_to_workdir->new_file.path))
+			found_parent_child1_file = 1;
+
+		if (!strcmp("parent/child2/file.txt", entry->index_to_workdir->new_file.path))
+			found_parent_child2_file = 1;
+	}
+	git_status_list_free(list);
+
+	cl_assert(found_parent_file);
+	cl_assert(found_parent_child1_file);
+	cl_assert(found_parent_child2_file);
+}
+