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diff --git a/changelog.d/8950.misc b/changelog.d/8950.misc
new file mode 100644
index 000000000..42e0335af
--- /dev/null
+++ b/changelog.d/8950.misc
@@ -0,0 +1 @@
+Add a maximum size of 50 kilobytes to .well-known lookups.
diff --git a/synapse/http/client.py b/synapse/http/client.py
index df7730078..29f40ddf5 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -720,11 +720,14 @@ class SimpleHttpClient:
 
         try:
             length = await make_deferred_yieldable(
-                readBodyToFile(response, output_stream, max_size)
+                read_body_with_max_size(response, output_stream, max_size)
+            )
+        except BodyExceededMaxSize:
+            SynapseError(
+                502,
+                "Requested file is too large > %r bytes" % (max_size,),
+                Codes.TOO_LARGE,
             )
-        except SynapseError:
-            # This can happen e.g. because the body is too large.
-            raise
         except Exception as e:
             raise SynapseError(502, ("Failed to download remote body: %s" % e)) from e
 
@@ -748,7 +751,11 @@ def _timeout_to_request_timed_out_error(f: Failure):
     return f
 
 
-class _ReadBodyToFileProtocol(protocol.Protocol):
+class BodyExceededMaxSize(Exception):
+    """The maximum allowed size of the HTTP body was exceeded."""
+
+
+class _ReadBodyWithMaxSizeProtocol(protocol.Protocol):
     def __init__(
         self, stream: BinaryIO, deferred: defer.Deferred, max_size: Optional[int]
     ):
@@ -761,13 +768,7 @@ class _ReadBodyToFileProtocol(protocol.Protocol):
         self.stream.write(data)
         self.length += len(data)
         if self.max_size is not None and self.length >= self.max_size:
-            self.deferred.errback(
-                SynapseError(
-                    502,
-                    "Requested file is too large > %r bytes" % (self.max_size,),
-                    Codes.TOO_LARGE,
-                )
-            )
+            self.deferred.errback(BodyExceededMaxSize())
             self.deferred = defer.Deferred()
             self.transport.loseConnection()
 
@@ -782,12 +783,15 @@ class _ReadBodyToFileProtocol(protocol.Protocol):
             self.deferred.errback(reason)
 
 
-def readBodyToFile(
+def read_body_with_max_size(
     response: IResponse, stream: BinaryIO, max_size: Optional[int]
 ) -> defer.Deferred:
     """
     Read a HTTP response body to a file-object. Optionally enforcing a maximum file size.
 
+    If the maximum file size is reached, the returned Deferred will resolve to a
+    Failure with a BodyExceededMaxSize exception.
+
     Args:
         response: The HTTP response to read from.
         stream: The file-object to write to.
@@ -798,7 +802,7 @@ def readBodyToFile(
     """
 
     d = defer.Deferred()
-    response.deliverBody(_ReadBodyToFileProtocol(stream, d, max_size))
+    response.deliverBody(_ReadBodyWithMaxSizeProtocol(stream, d, max_size))
     return d
 
 
diff --git a/synapse/http/federation/well_known_resolver.py b/synapse/http/federation/well_known_resolver.py
index 5e08ef166..b3b6dbcab 100644
--- a/synapse/http/federation/well_known_resolver.py
+++ b/synapse/http/federation/well_known_resolver.py
@@ -15,17 +15,19 @@
 import logging
 import random
 import time
+from io import BytesIO
 from typing import Callable, Dict, Optional, Tuple
 
 import attr
 
 from twisted.internet import defer
 from twisted.internet.interfaces import IReactorTime
-from twisted.web.client import RedirectAgent, readBody
+from twisted.web.client import RedirectAgent
 from twisted.web.http import stringToDatetime
 from twisted.web.http_headers import Headers
 from twisted.web.iweb import IAgent, IResponse
 
+from synapse.http.client import BodyExceededMaxSize, read_body_with_max_size
 from synapse.logging.context import make_deferred_yieldable
 from synapse.util import Clock, json_decoder
 from synapse.util.caches.ttlcache import TTLCache
@@ -53,6 +55,9 @@ WELL_KNOWN_MAX_CACHE_PERIOD = 48 * 3600
 # lower bound for .well-known cache period
 WELL_KNOWN_MIN_CACHE_PERIOD = 5 * 60
 
+# The maximum size (in bytes) to allow a well-known file to be.
+WELL_KNOWN_MAX_SIZE = 50 * 1024  # 50 KiB
+
 # Attempt to refetch a cached well-known N% of the TTL before it expires.
 # e.g. if set to 0.2 and we have a cached entry with a TTL of 5mins, then
 # we'll start trying to refetch 1 minute before it expires.
@@ -229,6 +234,9 @@ class WellKnownResolver:
             server_name: name of the server, from the requested url
             retry: Whether to retry the request if it fails.
 
+        Raises:
+            _FetchWellKnownFailure if we fail to lookup a result
+
         Returns:
             Returns the response object and body. Response may be a non-200 response.
         """
@@ -250,7 +258,11 @@ class WellKnownResolver:
                         b"GET", uri, headers=Headers(headers)
                     )
                 )
-                body = await make_deferred_yieldable(readBody(response))
+                body_stream = BytesIO()
+                await make_deferred_yieldable(
+                    read_body_with_max_size(response, body_stream, WELL_KNOWN_MAX_SIZE)
+                )
+                body = body_stream.getvalue()
 
                 if 500 <= response.code < 600:
                     raise Exception("Non-200 response %s" % (response.code,))
@@ -259,6 +271,15 @@ class WellKnownResolver:
             except defer.CancelledError:
                 # Bail if we've been cancelled
                 raise
+            except BodyExceededMaxSize:
+                # If the well-known file was too large, do not keep attempting
+                # to download it, but consider it a temporary error.
+                logger.warning(
+                    "Requested .well-known file for %s is too large > %r bytes",
+                    server_name.decode("ascii"),
+                    WELL_KNOWN_MAX_SIZE,
+                )
+                raise _FetchWellKnownFailure(temporary=True)
             except Exception as e:
                 if not retry or i >= WELL_KNOWN_RETRY_ATTEMPTS:
                     logger.info("Error fetching %s: %s", uri_str, e)
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index c96299472..b261e078c 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -37,16 +37,19 @@ from twisted.web.iweb import IBodyProducer, IResponse
 import synapse.metrics
 import synapse.util.retryutils
 from synapse.api.errors import (
+    Codes,
     FederationDeniedError,
     HttpResponseException,
     RequestSendFailed,
+    SynapseError,
 )
 from synapse.http import QuieterFileBodyProducer
 from synapse.http.client import (
     BlacklistingAgentWrapper,
     BlacklistingReactorWrapper,
+    BodyExceededMaxSize,
     encode_query_args,
-    readBodyToFile,
+    read_body_with_max_size,
 )
 from synapse.http.federation.matrix_federation_agent import MatrixFederationAgent
 from synapse.logging.context import make_deferred_yieldable
@@ -975,9 +978,15 @@ class MatrixFederationHttpClient:
         headers = dict(response.headers.getAllRawHeaders())
 
         try:
-            d = readBodyToFile(response, output_stream, max_size)
+            d = read_body_with_max_size(response, output_stream, max_size)
             d.addTimeout(self.default_timeout, self.reactor)
             length = await make_deferred_yieldable(d)
+        except BodyExceededMaxSize:
+            msg = "Requested file is too large > %r bytes" % (max_size,)
+            logger.warning(
+                "{%s} [%s] %s", request.txn_id, request.destination, msg,
+            )
+            SynapseError(502, msg, Codes.TOO_LARGE)
         except Exception as e:
             logger.warning(
                 "{%s} [%s] Error reading response: %s",
diff --git a/tests/http/federation/test_matrix_federation_agent.py b/tests/http/federation/test_matrix_federation_agent.py
index 626acdcaa..4e51839d0 100644
--- a/tests/http/federation/test_matrix_federation_agent.py
+++ b/tests/http/federation/test_matrix_federation_agent.py
@@ -36,6 +36,7 @@ from synapse.crypto.context_factory import FederationPolicyForHTTPS
 from synapse.http.federation.matrix_federation_agent import MatrixFederationAgent
 from synapse.http.federation.srv_resolver import Server
 from synapse.http.federation.well_known_resolver import (
+    WELL_KNOWN_MAX_SIZE,
     WellKnownResolver,
     _cache_period_from_headers,
 )
@@ -1107,6 +1108,32 @@ class MatrixFederationAgentTests(unittest.TestCase):
         r = self.successResultOf(fetch_d)
         self.assertEqual(r.delegated_server, None)
 
+    def test_well_known_too_large(self):
+        """A well-known query that returns a result which is too large should be rejected."""
+        self.reactor.lookups["testserv"] = "1.2.3.4"
+
+        fetch_d = defer.ensureDeferred(
+            self.well_known_resolver.get_well_known(b"testserv")
+        )
+
+        # there should be an attempt to connect on port 443 for the .well-known
+        clients = self.reactor.tcpClients
+        self.assertEqual(len(clients), 1)
+        (host, port, client_factory, _timeout, _bindAddress) = clients.pop(0)
+        self.assertEqual(host, "1.2.3.4")
+        self.assertEqual(port, 443)
+
+        self._handle_well_known_connection(
+            client_factory,
+            expected_sni=b"testserv",
+            response_headers={b"Cache-Control": b"max-age=1000"},
+            content=b'{ "m.server": "' + (b"a" * WELL_KNOWN_MAX_SIZE) + b'" }',
+        )
+
+        # The result is sucessful, but disabled delegation.
+        r = self.successResultOf(fetch_d)
+        self.assertIsNone(r.delegated_server)
+
     def test_srv_fallbacks(self):
         """Test that other SRV results are tried if the first one fails.
         """