Merge branch 'master' into develop

9 files changed, 229 insertions, 11 deletions

diff --git a/CHANGES.md b/CHANGES.md
index 2aebe92cac..db11de0e85 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,5 +1,30 @@
-Synapse 1.25.0rc1 (2021-01-06)
-==============================
+Synapse 1.25.0 (2021-01-13)
+===========================
+
+Ending Support for Python 3.5 and Postgres 9.5
+----------------------------------------------
+
+With this release, the Synapse team is announcing a formal deprecation policy for our platform dependencies, like Python and PostgreSQL:
+
+All future releases of Synapse will follow the upstream end-of-life schedules.
+
+Which means:
+
+* This is the last release which guarantees support for Python 3.5.
+* We will end support for PostgreSQL 9.5 early next month.
+* We will end support for Python 3.6 and PostgreSQL 9.6 near the end of the year.
+
+Crucially, this means __we will not produce .deb packages for Debian 9 (Stretch) or Ubuntu 16.04 (Xenial)__ beyond the transition period described below.
+
+The website https://endoflife.date/ has convenient summaries of the support schedules for projects like [Python](https://endoflife.date/python) and [PostgreSQL](https://endoflife.date/postgresql).
+
+If you are unable to upgrade your environment to a supported version of Python or Postgres, we encourage you to consider using the [Synapse Docker images](./INSTALL.md#docker-images-and-ansible-playbooks) instead.
+
+### Transition Period
+
+We will make a good faith attempt to avoid breaking compatibility in all releases through the end of March 2021. However, critical security vulnerabilities in dependencies or other unanticipated circumstances may arise which necessitate breaking compatibility earlier.
+
+We intend to continue producing .deb packages for Debian 9 (Stretch) and Ubuntu 16.04 (Xenial) through the transition period.
 
 Removal warning
 ---------------
@@ -12,6 +37,15 @@ are deprecated and will be removed in a future release. They will be replaced by
 `POST /_synapse/admin/v1/rooms/<room_id>/delete` replaces `POST /_synapse/admin/v1/purge_room` and
 `POST /_synapse/admin/v1/shutdown_room/<room_id>`.
 
+Bugfixes
+--------
+
+- Fix HTTP proxy support when using a proxy that is on a blacklisted IP. Introduced in v1.25.0rc1. Contributed by @Bubu. ([\#9084](https://github.com/matrix-org/synapse/issues/9084))
+
+
+Synapse 1.25.0rc1 (2021-01-06)
+==============================
+
 Features
 --------
 
@@ -61,7 +95,7 @@ Improved Documentation
 - Combine related media admin API docs. ([\#8839](https://github.com/matrix-org/synapse/issues/8839))
 - Fix an error in the documentation for the SAML username mapping provider. ([\#8873](https://github.com/matrix-org/synapse/issues/8873))
 - Clarify comments around template directories in `sample_config.yaml`. ([\#8891](https://github.com/matrix-org/synapse/issues/8891))
-- Moved instructions for database setup, adjusted heading levels and improved syntax highlighting in [INSTALL.md](../INSTALL.md). Contributed by fossterer. ([\#8987](https://github.com/matrix-org/synapse/issues/8987))
+- Move instructions for database setup, adjusted heading levels and improved syntax highlighting in [INSTALL.md](../INSTALL.md). Contributed by @fossterer. ([\#8987](https://github.com/matrix-org/synapse/issues/8987))
 - Update the example value of `group_creation_prefix` in the sample configuration. ([\#8992](https://github.com/matrix-org/synapse/issues/8992))
 - Link the Synapse developer room to the development section in the docs. ([\#9002](https://github.com/matrix-org/synapse/issues/9002))
 
diff --git a/UPGRADE.rst b/UPGRADE.rst
index 54a40bd42f..f750d17da2 100644
--- a/UPGRADE.rst
+++ b/UPGRADE.rst
@@ -5,6 +5,16 @@ Before upgrading check if any special steps are required to upgrade from the
 version you currently have installed to the current version of Synapse. The extra
 instructions that may be required are listed later in this document.
 
+* Check that your versions of Python and PostgreSQL are still supported.
+
+  Synapse follows upstream lifecycles for `Python`_ and `PostgreSQL`_, and
+  removes support for versions which are no longer maintained.
+
+  The website https://endoflife.date also offers convenient summaries.
+
+  .. _Python: https://devguide.python.org/devcycle/#end-of-life-branches
+  .. _PostgreSQL: https://www.postgresql.org/support/versioning/
+
 * If Synapse was installed using `prebuilt packages
   <INSTALL.md#prebuilt-packages>`_, you will need to follow the normal process
   for upgrading those packages.
@@ -78,6 +88,18 @@ for example:
 Upgrading to v1.25.0
 ====================
 
+Last release supporting Python 3.5
+----------------------------------
+
+This is the last release of Synapse which guarantees support with Python 3.5,
+which passed its upstream End of Life date several months ago.
+
+We will attempt to maintain support through March 2021, but without guarantees.
+
+In the future, Synapse will follow upstream schedules for ending support of
+older versions of Python and PostgreSQL. Please upgrade to at least Python 3.6
+and PostgreSQL 9.6 as soon as possible.
+
 Blacklisting IP ranges
 ----------------------
 
diff --git a/debian/changelog b/debian/changelog
index 6b819d201d..609436bf75 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,14 @@
+matrix-synapse-py3 (1.25.0) stable; urgency=medium
+
+  [ Dan Callahan ]
+  * Update dependencies to account for the removal of the transitional
+    dh-systemd package from Debian Bullseye.
+
+  [ Synapse Packaging team ]
+  * New synapse release 1.25.0.
+
+ -- Synapse Packaging team <packages@matrix.org>  Wed, 13 Jan 2021 10:14:55 +0000
+
 matrix-synapse-py3 (1.24.0) stable; urgency=medium
 
   * New synapse release 1.24.0.
diff --git a/debian/control b/debian/control
index bae14b41e4..b10401be43 100644
--- a/debian/control
+++ b/debian/control
@@ -3,9 +3,11 @@ Section: contrib/python
 Priority: extra
 Maintainer: Synapse Packaging team <packages@matrix.org>
 # keep this list in sync with the build dependencies in docker/Dockerfile-dhvirtualenv.
+# TODO: Remove the dependency on dh-systemd after dropping support for Ubuntu xenial
+#       On all other supported releases, it's merely a transitional package which
+#       does nothing but depends on debhelper (> 9.20160709)
 Build-Depends:
- debhelper (>= 9),
- dh-systemd,
+ debhelper (>= 9.20160709) | dh-systemd,
  dh-virtualenv (>= 1.1),
  libsystemd-dev,
  libpq-dev,
diff --git a/docker/Dockerfile-dhvirtualenv b/docker/Dockerfile-dhvirtualenv
index 2b7f01f7f7..e529293803 100644
--- a/docker/Dockerfile-dhvirtualenv
+++ b/docker/Dockerfile-dhvirtualenv
@@ -50,17 +50,22 @@ FROM ${distro}
 ARG distro=""
 ENV distro ${distro}
 
+# Python < 3.7 assumes LANG="C" means ASCII-only and throws on printing unicode
+# http://bugs.python.org/issue19846
+ENV LANG C.UTF-8
+
 # Install the build dependencies
 #
 # NB: keep this list in sync with the list of build-deps in debian/control
 # TODO: it would be nice to do that automatically.
+# TODO: Remove the dh-systemd stanza after dropping support for Ubuntu xenial
+#       it's a transitional package on all other, more recent releases
 RUN apt-get update -qq -o Acquire::Languages=none \
     && env DEBIAN_FRONTEND=noninteractive apt-get install \
         -yqq --no-install-recommends -o Dpkg::Options::=--force-unsafe-io \
         build-essential \
         debhelper \
         devscripts \
-        dh-systemd \
         libsystemd-dev \
         lsb-release \
         pkg-config \
@@ -70,7 +75,10 @@ RUN apt-get update -qq -o Acquire::Languages=none \
         python3-venv \
         sqlite3 \
         libpq-dev \
-        xmlsec1
+        xmlsec1 \
+    && ( env DEBIAN_FRONTEND=noninteractive apt-get install \
+         -yqq --no-install-recommends -o Dpkg::Options::=--force-unsafe-io \
+         dh-systemd || true )
 
 COPY --from=builder /dh-virtualenv_1.2~dev-1_all.deb /
 
diff --git a/synapse/__init__.py b/synapse/__init__.py
index 99fb675748..193adca624 100644
--- a/synapse/__init__.py
+++ b/synapse/__init__.py
@@ -48,7 +48,7 @@ try:
 except ImportError:
     pass
 
-__version__ = "1.25.0rc1"
+__version__ = "1.25.0"
 
 if bool(os.environ.get("SYNAPSE_TEST_PATCH_LOG_CONTEXTS", False)):
     # We import here so that we don't have to install a bunch of deps when
diff --git a/synapse/http/client.py b/synapse/http/client.py
index 29f40ddf5f..5f74ee1149 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -341,6 +341,7 @@ class SimpleHttpClient:
 
         self.agent = ProxyAgent(
             self.reactor,
+            hs.get_reactor(),
             connectTimeout=15,
             contextFactory=self.hs.get_http_client_context_factory(),
             pool=pool,
diff --git a/synapse/http/proxyagent.py b/synapse/http/proxyagent.py
index e32d3f43e0..b730d2c634 100644
--- a/synapse/http/proxyagent.py
+++ b/synapse/http/proxyagent.py
@@ -39,6 +39,10 @@ class ProxyAgent(_AgentBase):
         reactor: twisted reactor to place outgoing
             connections.
 
+        proxy_reactor: twisted reactor to use for connections to the proxy server
+                       reactor might have some blacklisting applied (i.e. for DNS queries),
+                       but we need unblocked access to the proxy.
+
         contextFactory (IPolicyForHTTPS): A factory for TLS contexts, to control the
             verification parameters of OpenSSL.  The default is to use a
             `BrowserLikePolicyForHTTPS`, so unless you have special
@@ -59,6 +63,7 @@ class ProxyAgent(_AgentBase):
     def __init__(
         self,
         reactor,
+        proxy_reactor=None,
         contextFactory=BrowserLikePolicyForHTTPS(),
         connectTimeout=None,
         bindAddress=None,
@@ -68,6 +73,11 @@ class ProxyAgent(_AgentBase):
     ):
         _AgentBase.__init__(self, reactor, pool)
 
+        if proxy_reactor is None:
+            self.proxy_reactor = reactor
+        else:
+            self.proxy_reactor = proxy_reactor
+
         self._endpoint_kwargs = {}
         if connectTimeout is not None:
             self._endpoint_kwargs["timeout"] = connectTimeout
@@ -75,11 +85,11 @@ class ProxyAgent(_AgentBase):
             self._endpoint_kwargs["bindAddress"] = bindAddress
 
         self.http_proxy_endpoint = _http_proxy_endpoint(
-            http_proxy, reactor, **self._endpoint_kwargs
+            http_proxy, self.proxy_reactor, **self._endpoint_kwargs
         )
 
         self.https_proxy_endpoint = _http_proxy_endpoint(
-            https_proxy, reactor, **self._endpoint_kwargs
+            https_proxy, self.proxy_reactor, **self._endpoint_kwargs
         )
 
         self._policy_for_https = contextFactory
@@ -137,7 +147,7 @@ class ProxyAgent(_AgentBase):
             request_path = uri
         elif parsed_uri.scheme == b"https" and self.https_proxy_endpoint:
             endpoint = HTTPConnectProxyEndpoint(
-                self._reactor,
+                self.proxy_reactor,
                 self.https_proxy_endpoint,
                 parsed_uri.host,
                 parsed_uri.port,
diff --git a/tests/http/test_proxyagent.py b/tests/http/test_proxyagent.py
index 22abf76515..9a56e1c14a 100644
--- a/tests/http/test_proxyagent.py
+++ b/tests/http/test_proxyagent.py
@@ -15,12 +15,14 @@
 import logging
 
 import treq
+from netaddr import IPSet
 
 from twisted.internet import interfaces  # noqa: F401
 from twisted.internet.protocol import Factory
 from twisted.protocols.tls import TLSMemoryBIOFactory
 from twisted.web.http import HTTPChannel
 
+from synapse.http.client import BlacklistingReactorWrapper
 from synapse.http.proxyagent import ProxyAgent
 
 from tests.http import TestServerTLSConnectionFactory, get_test_https_policy
@@ -292,6 +294,134 @@ class MatrixFederationAgentTests(TestCase):
         body = self.successResultOf(treq.content(resp))
         self.assertEqual(body, b"result")
 
+    def test_http_request_via_proxy_with_blacklist(self):
+        # The blacklist includes the configured proxy IP.
+        agent = ProxyAgent(
+            BlacklistingReactorWrapper(
+                self.reactor, ip_whitelist=None, ip_blacklist=IPSet(["1.0.0.0/8"])
+            ),
+            self.reactor,
+            http_proxy=b"proxy.com:8888",
+        )
+
+        self.reactor.lookups["proxy.com"] = "1.2.3.5"
+        d = agent.request(b"GET", b"http://test.com")
+
+        # there should be a pending TCP connection
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[0]
+        self.assertEqual(host, "1.2.3.5")
+        self.assertEqual(port, 8888)
+
+        # make a test server, and wire up the client
+        http_server = self._make_connection(
+            client_factory, _get_test_protocol_factory()
+        )
+
+        # the FakeTransport is async, so we need to pump the reactor
+        self.reactor.advance(0)
+
+        # now there should be a pending request
+        self.assertEqual(len(http_server.requests), 1)
+
+        request = http_server.requests[0]
+        self.assertEqual(request.method, b"GET")
+        self.assertEqual(request.path, b"http://test.com")
+        self.assertEqual(request.requestHeaders.getRawHeaders(b"host"), [b"test.com"])
+        request.write(b"result")
+        request.finish()
+
+        self.reactor.advance(0)
+
+        resp = self.successResultOf(d)
+        body = self.successResultOf(treq.content(resp))
+        self.assertEqual(body, b"result")
+
+    def test_https_request_via_proxy_with_blacklist(self):
+        # The blacklist includes the configured proxy IP.
+        agent = ProxyAgent(
+            BlacklistingReactorWrapper(
+                self.reactor, ip_whitelist=None, ip_blacklist=IPSet(["1.0.0.0/8"])
+            ),
+            self.reactor,
+            contextFactory=get_test_https_policy(),
+            https_proxy=b"proxy.com",
+        )
+
+        self.reactor.lookups["proxy.com"] = "1.2.3.5"
+        d = agent.request(b"GET", b"https://test.com/abc")
+
+        # there should be a pending TCP connection
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients[0]
+        self.assertEqual(host, "1.2.3.5")
+        self.assertEqual(port, 1080)
+
+        # make a test HTTP server, and wire up the client
+        proxy_server = self._make_connection(
+            client_factory, _get_test_protocol_factory()
+        )
+
+        # fish the transports back out so that we can do the old switcheroo
+        s2c_transport = proxy_server.transport
+        client_protocol = s2c_transport.other
+        c2s_transport = client_protocol.transport
+
+        # the FakeTransport is async, so we need to pump the reactor
+        self.reactor.advance(0)
+
+        # now there should be a pending CONNECT request
+        self.assertEqual(len(proxy_server.requests), 1)
+
+        request = proxy_server.requests[0]
+        self.assertEqual(request.method, b"CONNECT")
+        self.assertEqual(request.path, b"test.com:443")
+
+        # tell the proxy server not to close the connection
+        proxy_server.persistent = True
+
+        # this just stops the http Request trying to do a chunked response
+        # request.setHeader(b"Content-Length", b"0")
+        request.finish()
+
+        # now we can replace the proxy channel with a new, SSL-wrapped HTTP channel
+        ssl_factory = _wrap_server_factory_for_tls(_get_test_protocol_factory())
+        ssl_protocol = ssl_factory.buildProtocol(None)
+        http_server = ssl_protocol.wrappedProtocol
+
+        ssl_protocol.makeConnection(
+            FakeTransport(client_protocol, self.reactor, ssl_protocol)
+        )
+        c2s_transport.other = ssl_protocol
+
+        self.reactor.advance(0)
+
+        server_name = ssl_protocol._tlsConnection.get_servername()
+        expected_sni = b"test.com"
+        self.assertEqual(
+            server_name,
+            expected_sni,
+            "Expected SNI %s but got %s" % (expected_sni, server_name),
+        )
+
+        # now there should be a pending request
+        self.assertEqual(len(http_server.requests), 1)
+
+        request = http_server.requests[0]
+        self.assertEqual(request.method, b"GET")
+        self.assertEqual(request.path, b"/abc")
+        self.assertEqual(request.requestHeaders.getRawHeaders(b"host"), [b"test.com"])
+        request.write(b"result")
+        request.finish()
+
+        self.reactor.advance(0)
+
+        resp = self.successResultOf(d)
+        body = self.successResultOf(treq.content(resp))
+        self.assertEqual(body, b"result")
+
 
 def _wrap_server_factory_for_tls(factory, sanlist=None):
     """Wrap an existing Protocol Factory with a test TLSMemoryBIOFactory