diff --git a/ui/sort.go b/ui/sort.go
index 4f389fb..5387e75 100644
--- a/ui/sort.go
+++ b/ui/sort.go
@@ -2,11 +2,24 @@ package ui
 
 import (
 	"cmp"
+	"path/filepath"
 	"slices"
+	"strings"
 )
 
 func sortMarkdowns(mds []*markdown) {
 	slices.SortStableFunc(mds, func(a, b *markdown) int {
+		if n := cmp.Compare(markdownPathDepth(a.Note), markdownPathDepth(b.Note)); n != 0 {
+			return n
+		}
 		return cmp.Compare(a.Note, b.Note)
 	})
 }
+
+func markdownPathDepth(path string) int {
+	path = filepath.ToSlash(filepath.Clean(path))
+	if path == "." {
+		return 0
+	}
+	return strings.Count(path, "/")
+}
diff --git a/ui/sort_test.go b/ui/sort_test.go
new file mode 100644
index 0000000..3185850
--- /dev/null
+++ b/ui/sort_test.go
@@ -0,0 +1,33 @@
+package ui
+
+import "testing"
+
+func TestSortMarkdownsOrdersByDirectoryDepth(t *testing.T) {
+	mds := []*markdown{
+		{Note: "docs/reference/api.md"},
+		{Note: "docs/guide.md"},
+		{Note: "README.md"},
+		{Note: "CONTRIBUTING.md"},
+		{Note: "docs/reference/cli.md"},
+	}
+
+	sortMarkdowns(mds)
+
+	got := make([]string, 0, len(mds))
+	for _, md := range mds {
+		got = append(got, md.Note)
+	}
+
+	want := []string{
+		"CONTRIBUTING.md",
+		"README.md",
+		"docs/guide.md",
+		"docs/reference/api.md",
+		"docs/reference/cli.md",
+	}
+	for i := range want {
+		if got[i] != want[i] {
+			t.Fatalf("expected %v, got %v", want, got)
+		}
+	}
+}