diff --git a/roles/matrix/tasks/main.yml b/roles/matrix/tasks/main.yml
index a658a40aff6ee426c1f1c7a1834fe7aeeeea1405..10e04491270cbfa8c78390c1c8e40cb802495a32 100644
--- a/roles/matrix/tasks/main.yml
+++ b/roles/matrix/tasks/main.yml
@@ -78,7 +78,7 @@
 - name: install synapse
   pip:
     name:
-      - 'matrix-synapse[postgres,systemd,url_preview,redis,oidc]==1.37.1'
+      - 'matrix-synapse[postgres,systemd,url_preview,redis,oidc]==1.38.1'
     state: latest
     extra_args: '--upgrade-strategy=eager'
     virtualenv: /var/lib/synapse/venv
diff --git a/roles/matrix/templates/homeserver.yaml.j2 b/roles/matrix/templates/homeserver.yaml.j2
index 01a4198041134228997cdd1380ddf575343e94e3..bf195487311a4e01ccd6a6b2859792b9052b0616 100644
--- a/roles/matrix/templates/homeserver.yaml.j2
+++ b/roles/matrix/templates/homeserver.yaml.j2
@@ -26,7 +26,7 @@
 
 # Server admins can expand Synapse's functionality with external modules.
 #
-# See https://matrix-org.github.io/synapse/develop/modules.html for more
+# See https://matrix-org.github.io/synapse/latest/modules.html for more
 # documentation on how to configure or create custom modules for Synapse.
 #
 modules:
@@ -59,7 +59,7 @@ spam_checker:
 # In most cases you should avoid using a matrix specific subdomain such as
 # matrix.example.com or synapse.example.com as the server_name for the same
 # reasons you wouldn't use user@email.example.com as your email address.
-# See https://github.com/matrix-org/synapse/blob/master/docs/delegate.md
+# See https://matrix-org.github.io/synapse/latest/delegate.html
 # for information on how to host Synapse on a subdomain while preserving
 # a clean server_name.
 #
@@ -254,9 +254,9 @@ allow_public_rooms_over_federation: true
 #       'all local interfaces'.
 #
 #   type: the type of listener. Normally 'http', but other valid options are:
-#       'manhole' (see docs/manhole.md),
-#       'metrics' (see docs/metrics-howto.md),
-#       'replication' (see docs/workers.md).
+#       'manhole' (see https://matrix-org.github.io/synapse/latest/manhole.html),
+#       'metrics' (see https://matrix-org.github.io/synapse/latest/metrics-howto.html),
+#       'replication' (see https://matrix-org.github.io/synapse/latest/workers.html).
 #
 #   tls: set to true to enable TLS for this listener. Will use the TLS
 #       key/cert specified in tls_private_key_path / tls_certificate_path.
@@ -281,8 +281,8 @@ allow_public_rooms_over_federation: true
 #   client: the client-server API (/_matrix/client), and the synapse admin
 #       API (/_synapse/admin). Also implies 'media' and 'static'.
 #
-#   consent: user consent forms (/_matrix/consent). See
-#       docs/consent_tracking.md.
+#   consent: user consent forms (/_matrix/consent).
+#       See https://matrix-org.github.io/synapse/latest/consent_tracking.html.
 #
 #   federation: the server-server API (/_matrix/federation). Also implies
 #       'media', 'keys', 'openid'
@@ -291,12 +291,13 @@ allow_public_rooms_over_federation: true
 #
 #   media: the media API (/_matrix/media).
 #
-#   metrics: the metrics interface. See docs/metrics-howto.md.
+#   metrics: the metrics interface.
+#       See https://matrix-org.github.io/synapse/latest/metrics-howto.html.
 #
 #   openid: OpenID authentication.
 #
-#   replication: the HTTP replication API (/_synapse/replication). See
-#       docs/workers.md.
+#   replication: the HTTP replication API (/_synapse/replication).
+#       See https://matrix-org.github.io/synapse/latest/workers.html.
 #
 #   static: static resources under synapse/static (/_matrix/static). (Mostly
 #       useful for 'fallback authentication'.)
@@ -320,7 +321,7 @@ listeners:
   # that unwraps TLS.
   #
   # If you plan to use a reverse proxy, please see
-  # https://github.com/matrix-org/synapse/blob/master/docs/reverse_proxy.md.
+  # https://matrix-org.github.io/synapse/latest/reverse_proxy.html.
   #
   - port: 8008
     tls: false
@@ -685,35 +686,41 @@ federation_metrics_domains:
 #event_cache_size: 10K
 
 caches:
-   # Controls the global cache factor, which is the default cache factor
-   # for all caches if a specific factor for that cache is not otherwise
-   # set.
-   #
-   # This can also be set by the "SYNAPSE_CACHE_FACTOR" environment
-   # variable. Setting by environment variable takes priority over
-   # setting through the config file.
-   #
-   # Defaults to 0.5, which will half the size of all caches.
-   #
-   global_factor: 0.7
+  # Controls the global cache factor, which is the default cache factor
+  # for all caches if a specific factor for that cache is not otherwise
+  # set.
+  #
+  # This can also be set by the "SYNAPSE_CACHE_FACTOR" environment
+  # variable. Setting by environment variable takes priority over
+  # setting through the config file.
+  #
+  # Defaults to 0.5, which will half the size of all caches.
+  #
+  global_factor: 0.7
 
-   # A dictionary of cache name to cache factor for that individual
-   # cache. Overrides the global cache factor for a given cache.
-   #
-   # These can also be set through environment variables comprised
-   # of "SYNAPSE_CACHE_FACTOR_" + the name of the cache in capital
-   # letters and underscores. Setting by environment variable
-   # takes priority over setting through the config file.
-   # Ex. SYNAPSE_CACHE_FACTOR_GET_USERS_WHO_SHARE_ROOM_WITH_USER=2.0
-   #
-   # Some caches have '*' and other characters that are not
-   # alphanumeric or underscores. These caches can be named with or
-   # without the special characters stripped. For example, to specify
-   # the cache factor for `*stateGroupCache*` via an environment
-   # variable would be `SYNAPSE_CACHE_FACTOR_STATEGROUPCACHE=2.0`.
-   #
-   per_cache_factors:
-     #get_users_who_share_room_with_user: 2.0
+  # A dictionary of cache name to cache factor for that individual
+  # cache. Overrides the global cache factor for a given cache.
+  #
+  # These can also be set through environment variables comprised
+  # of "SYNAPSE_CACHE_FACTOR_" + the name of the cache in capital
+  # letters and underscores. Setting by environment variable
+  # takes priority over setting through the config file.
+  # Ex. SYNAPSE_CACHE_FACTOR_GET_USERS_WHO_SHARE_ROOM_WITH_USER=2.0
+  #
+  # Some caches have '*' and other characters that are not
+  # alphanumeric or underscores. These caches can be named with or
+  # without the special characters stripped. For example, to specify
+  # the cache factor for `*stateGroupCache*` via an environment
+  # variable would be `SYNAPSE_CACHE_FACTOR_STATEGROUPCACHE=2.0`.
+  #
+  per_cache_factors:
+    #get_users_who_share_room_with_user: 2.0
+
+  # Controls how long an entry can be in a cache without having been
+  # accessed before being evicted. Defaults to None, which means
+  # entries are never evicted based on time.
+  #
+  expiry_time: 1h
 
 
 ## Database ##
@@ -753,7 +760,8 @@ caches:
 #    cp_min: 5
 #    cp_max: 10
 #
-# For more information on using Synapse with Postgres, see `docs/postgres.md`.
+# For more information on using Synapse with Postgres,
+# see https://matrix-org.github.io/synapse/latest/postgres.html.
 #
 database:
   name: psycopg2
@@ -807,9 +815,9 @@ worker_log_config: "/etc/synapse/log_config.yaml"
 #
 # The defaults are as shown below.
 #
-rc_message:
-  per_second: 0.5
-  burst_count: 20
+#rc_message:
+#  per_second: 0.2
+#  burst_count: 10
 #
 #rc_registration:
 #  per_second: 0.17
@@ -909,6 +917,10 @@ media_store_path: "/var/lib/synapse/media_store"
 
 # The largest allowed upload size in bytes
 #
+# If you are using a reverse proxy you may also need to set this value in
+# your reverse proxy's config. Notably Nginx has a small max body size by default.
+# See https://matrix-org.github.io/synapse/latest/reverse_proxy.html.
+#
 max_upload_size: {{ matrix_max_upload_size }}
 
 # Maximum number of pixels that will be thumbnailed
@@ -1851,7 +1863,7 @@ saml2_config:
 #
 #       module: The class name of a custom mapping module. Default is
 #           'synapse.handlers.oidc.JinjaOidcMappingProvider'.
-#           See https://github.com/matrix-org/synapse/blob/master/docs/sso_mapping_providers.md#openid-mapping-providers
+#           See https://matrix-org.github.io/synapse/latest/sso_mapping_providers.html#openid-mapping-providers
 #           for information on implementing a custom mapping provider.
 #
 #       config: Configuration for the mapping provider module. This section will
@@ -1902,7 +1914,7 @@ saml2_config:
 #     - attribute: groups
 #       value: "admin"
 #
-# See https://github.com/matrix-org/synapse/blob/master/docs/openid.md
+# See https://matrix-org.github.io/synapse/latest/openid.html
 # for information on how to configure these options.
 #
 # For backwards compatibility, it is also possible to configure a single OIDC
@@ -2200,7 +2212,7 @@ sso:
 # Note that this is a non-standard login type and client support is
 # expected to be non-existent.
 #
-# See https://github.com/matrix-org/synapse/blob/master/docs/jwt.md.
+# See https://matrix-org.github.io/synapse/latest/jwt.html.
 #
 #jwt_config:
     # Uncomment the following to enable authorization using JSON web
@@ -2500,7 +2512,7 @@ email:
 # ex. LDAP, external tokens, etc.
 #
 # For more information and known implementations, please see
-# https://github.com/matrix-org/synapse/blob/master/docs/password_auth_providers.md
+# https://matrix-org.github.io/synapse/latest/password_auth_providers.html
 #
 # Note: instances wishing to use SAML or CAS authentication should
 # instead use the `saml2_config` or `cas_config` options,
@@ -2602,7 +2614,7 @@ user_directory:
     #
     # If you set it true, you'll have to rebuild the user_directory search
     # indexes, see:
-    # https://github.com/matrix-org/synapse/blob/master/docs/user_directory.md
+    # https://matrix-org.github.io/synapse/latest/user_directory.html
     #
     # Uncomment to return search results containing all known users, even if that
     # user does not share a room with the requester.
@@ -2622,7 +2634,7 @@ user_directory:
 # User Consent configuration
 #
 # for detailed instructions, see
-# https://github.com/matrix-org/synapse/blob/master/docs/consent_tracking.md
+# https://matrix-org.github.io/synapse/latest/consent_tracking.html
 #
 # Parts of this section are required if enabling the 'consent' resource under
 # 'listeners', in particular 'template_dir' and 'version'.
@@ -2672,7 +2684,7 @@ user_directory:
 
 
 # Settings for local room and user statistics collection. See
-# docs/room_and_user_statistics.md.
+# https://matrix-org.github.io/synapse/latest/room_and_user_statistics.html.
 #
 stats:
   # Uncomment the following to disable room and user statistics. Note that doing
@@ -2799,7 +2811,7 @@ opentracing:
     #enabled: true
 
     # The list of homeservers we wish to send and receive span contexts and span baggage.
-    # See docs/opentracing.rst.
+    # See https://matrix-org.github.io/synapse/latest/opentracing.html.
     #
     # This is a list of regexes which are matched against the server_name of the
     # homeserver.