diff --git a/cheroot/test/test_wsgi.py b/cheroot/test/test_wsgi.py
index e546213dee..ca9f2b9b48 100644
--- a/cheroot/test/test_wsgi.py
+++ b/cheroot/test/test_wsgi.py
@@ -1,9 +1,13 @@
 """Test wsgi."""
 
 import threading
+from concurrent.futures.thread import ThreadPoolExecutor
 
 import pytest
 import portend
+import requests
+from requests_toolbelt.sessions import BaseUrlSession as Session
+from jaraco.context import ExceptionTrap
 
 from cheroot import wsgi
 
@@ -25,6 +29,7 @@ def app(environ, start_response):
     thread = threading.Thread(target=server.start)
     thread.setDaemon(True)
     thread.start()
+    url = 'http://localhost:{port}/'.format(**locals())
     yield locals()
     # would prefer to stop server, but has errors
     # server.stop()
@@ -32,4 +37,23 @@ def app(environ, start_response):
 
 def test_connection_keepalive(simple_wsgi_server):
     """Test the connection keepalive works (duh)."""
-    pass
+    session = Session(base_url=simple_wsgi_server['url'])
+    pooled = requests.adapters.HTTPAdapter(
+        pool_connections=1, pool_maxsize=1000,
+    )
+    session.mount('http://', pooled)
+
+    def do_request():
+        with ExceptionTrap(requests.exceptions.ConnectionError) as trap:
+            resp = session.get('info')
+            resp.raise_for_status()
+        return bool(trap)
+
+    with ThreadPoolExecutor(max_workers=50) as pool:
+        tasks = [
+            pool.submit(do_request)
+            for n in range(1000)
+        ]
+        failures = sum(task.result() for task in tasks)
+
+    assert not failures
diff --git a/setup.cfg b/setup.cfg
index 99adb7d478..6b066d796f 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -124,6 +124,8 @@ testing =
     colorama!=0.4.2; python_version == "3.4"
 
     portend
+    requests_toolbelt
+    jaraco.context
 
 [options.entry_points]
 console_scripts =