diff --git a/tests/test_staticfiles.py b/tests/test_staticfiles.py
index cdc119fba..ae694bab0 100644
--- a/tests/test_staticfiles.py
+++ b/tests/test_staticfiles.py
@@ -1,6 +1,7 @@
 import os
 import pathlib
 import stat
+import tempfile
 import time
 
 import anyio
@@ -454,15 +455,13 @@ def test_staticfiles_follows_symlinks(tmpdir, test_client_factory):
     statics_path = os.path.join(tmpdir, "statics")
     os.mkdir(statics_path)
 
-    symlink_path = os.path.join(tmpdir, "symlink")
-    os.mkdir(symlink_path)
-
-    symlink_file_path = os.path.join(symlink_path, "index.html")
-    with open(symlink_file_path, "w") as file:
+    source_path = tempfile.mkdtemp()
+    source_file_path = os.path.join(source_path, "page.html")
+    with open(source_file_path, "w") as file:
         file.write("<h1>Hello</h1>")
 
     statics_file_path = os.path.join(statics_path, "index.html")
-    os.symlink(symlink_file_path, statics_file_path)
+    os.symlink(source_file_path, statics_file_path)
 
     app = StaticFiles(directory=statics_path)
     client = test_client_factory(app)
@@ -473,19 +472,39 @@ def test_staticfiles_follows_symlinks(tmpdir, test_client_factory):
     assert response.text == "<h1>Hello</h1>"
 
 
-def test_staticfiles_disallows_path_traversal_with_symlinks(tmpdir):
+def test_staticfiles_follows_symlink_directories(tmpdir, test_client_factory):
     statics_path = os.path.join(tmpdir, "statics")
+    statics_html_path = os.path.join(statics_path, "html")
     os.mkdir(statics_path)
 
-    symlink_path = os.path.join(tmpdir, "symlink")
-    os.mkdir(symlink_path)
+    source_path = tempfile.mkdtemp()
+    source_file_path = os.path.join(source_path, "page.html")
+    with open(source_file_path, "w") as file:
+        file.write("<h1>Hello</h1>")
+
+    os.symlink(source_path, statics_html_path)
+
+    app = StaticFiles(directory=statics_path)
+    client = test_client_factory(app)
+
+    response = client.get("/html/page.html")
+    assert response.url == "http://testserver/html/page.html"
+    assert response.status_code == 200
+    assert response.text == "<h1>Hello</h1>"
+
+
+def test_staticfiles_disallows_path_traversal_with_symlinks(tmpdir):
+    statics_path = os.path.join(tmpdir, "statics")
+
+    root_source_path = tempfile.mkdtemp()
+    source_path = os.path.join(root_source_path, "statics")
+    os.mkdir(source_path)
 
-    symlink_file_path = os.path.join(symlink_path, "index.html")
-    with open(symlink_file_path, "w") as file:
+    source_file_path = os.path.join(root_source_path, "index.html")
+    with open(source_file_path, "w") as file:
         file.write("<h1>Hello</h1>")
 
-    temp_path = os.path.join(tmpdir, "index.html")
-    os.symlink(symlink_file_path, temp_path)
+    os.symlink(source_path, statics_path)
 
     app = StaticFiles(directory=statics_path)
     # We can't test this with 'requests', so we test the app directly here.