diff --git a/requirements-dev.txt b/requirements-dev.txt
index 6edee41781..1058ffb0ee 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -5,6 +5,7 @@ pytest-httpbin==1.0.0
 pytest-mock==2.0.0
 httpbin==0.7.0
 trustme
+Werkzeug
 wheel
 
 # Flask Stack
diff --git a/tests/test_lowlevel.py b/tests/test_lowlevel.py
index 859d07e8a5..2079b4d62e 100644
--- a/tests/test_lowlevel.py
+++ b/tests/test_lowlevel.py
@@ -2,6 +2,7 @@
 
 import pytest
 from tests.testserver.server import Server, consume_socket_content
+from tests.testserver.werkzeug_server import WerkzeugServer
 
 import requests
 from requests.compat import JSONDecodeError
@@ -23,17 +24,16 @@ def echo_response_handler(sock):
 
 def test_chunked_upload():
     """can safely send generators"""
-    close_server = threading.Event()
-    server = Server.basic_response_server(wait_to_close_event=close_server)
-    data = iter([b"a", b"b", b"c"])
+    server = WerkzeugServer.echo_server()
+    data = iter([b'a', b'b', b'c'])
 
     with server as (host, port):
-        url = f"http://{host}:{port}/"
+        url = f'http://{host}:{port}/'
         r = requests.post(url, data=data, stream=True)
-        close_server.set()  # release server block
 
+    assert r.content == b'abc'
     assert r.status_code == 200
-    assert r.request.headers["Transfer-Encoding"] == "chunked"
+    assert r.request.headers['Transfer-Encoding'] == 'chunked'
 
 
 def test_chunked_encoding_error():
diff --git a/tests/testserver/werkzeug_server.py b/tests/testserver/werkzeug_server.py
new file mode 100644
index 0000000000..ef8903a675
--- /dev/null
+++ b/tests/testserver/werkzeug_server.py
@@ -0,0 +1,55 @@
+import multiprocessing
+import socket
+from contextlib import closing
+
+from werkzeug import Request, Response, run_simple
+
+
+@Request.application
+def echo_application(request):
+    return Response(request.get_data(), 200, content_type=request.content_type)
+
+
+class WerkzeugServer:
+    """Realistic WSGI server for unit testing."""
+
+    SOCKET_CONNECT_TIMEOUT = 2
+
+    def __init__(self, application, host="localhost", port=0):
+        super().__init__()
+
+        self.host = host
+        self.port = port
+
+        # Werkzeug will not automatically pick a valid port for us.
+        if not self.port:
+            with closing(socket.socket()) as sock:
+                sock.bind((self.host, self.port))
+                self.port = sock.getsockname()[1]
+
+        self.process = multiprocessing.Process(
+            target=run_simple, args=(self.host, self.port, application)
+        )
+
+    @classmethod
+    def echo_server(cls):
+        return WerkzeugServer(echo_application)
+
+    def _socket_is_ready(self):
+        with closing(socket.socket()) as sock:
+            sock.settimeout(self.SOCKET_CONNECT_TIMEOUT)
+            return sock.connect_ex((self.host, self.port)) == 0
+
+    def __enter__(self):
+        self.process.start()
+
+        # Confirm that we can actually connect to the socket before we return.
+        # This protects from flaky tests should the process come up too late.
+        while not self._socket_is_ready():
+            pass
+
+        return self.host, self.port
+
+    def __exit__(self, exc_type, exc_value, traceback):
+        self.process.terminate()
+        return False