diff --git a/tests/http/test_site.py b/tests/http/test_site.py
new file mode 100644
index 0000000000..8c13b4f693
--- /dev/null
+++ b/tests/http/test_site.py
@@ -0,0 +1,83 @@
+# Copyright 2021 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+# http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+from twisted.internet.address import IPv6Address
+from twisted.test.proto_helpers import StringTransport
+
+from synapse.app.homeserver import SynapseHomeServer
+
+from tests.unittest import HomeserverTestCase
+
+
+class SynapseRequestTestCase(HomeserverTestCase):
+ def make_homeserver(self, reactor, clock):
+ return self.setup_test_homeserver(homeserver_to_use=SynapseHomeServer)
+
+ def test_large_request(self):
+ """overlarge HTTP requests should be rejected"""
+ self.hs.start_listening()
+
+ # find the HTTP server which is configured to listen on port 0
+ (port, factory, _backlog, interface) = self.reactor.tcpServers[0]
+ self.assertEqual(interface, "::")
+ self.assertEqual(port, 0)
+
+ # as a control case, first send a regular request.
+
+ # complete the connection and wire it up to a fake transport
+ client_address = IPv6Address("TCP", "::1", "2345")
+ protocol = factory.buildProtocol(client_address)
+ transport = StringTransport()
+ protocol.makeConnection(transport)
+
+ protocol.dataReceived(
+ b"POST / HTTP/1.1\r\n"
+ b"Connection: close\r\n"
+ b"Transfer-Encoding: chunked\r\n"
+ b"\r\n"
+ b"0\r\n"
+ b"\r\n"
+ )
+
+ while not transport.disconnecting:
+ self.reactor.advance(1)
+
+ # we should get a 404
+ self.assertRegex(transport.value().decode(), r"^HTTP/1\.1 404 ")
+
+ # now send an oversized request
+ protocol = factory.buildProtocol(client_address)
+ transport = StringTransport()
+ protocol.makeConnection(transport)
+
+ protocol.dataReceived(
+ b"POST / HTTP/1.1\r\n"
+ b"Connection: close\r\n"
+ b"Transfer-Encoding: chunked\r\n"
+ b"\r\n"
+ )
+
+ # we deliberately send all the data in one big chunk, to ensure that
+ # twisted isn't buffering the data in the chunked transfer decoder.
+ # we start with the chunk size, in hex. (We won't actually send this much)
+ protocol.dataReceived(b"10000000\r\n")
+ sent = 0
+ while not transport.disconnected:
+ self.assertLess(sent, 0x10000000, "connection did not drop")
+ protocol.dataReceived(b"\0" * 1024)
+ sent += 1024
+
+ # default max upload size is 50M, so it should drop on the next buffer after
+ # that.
+ self.assertEqual(sent, 50 * 1024 * 1024 + 1024)
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