diff --git a/CHANGELOG b/CHANGELOG
index da1ae02..3b00cea 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -559,3 +559,18 @@
 * Add a module callback to set username at registration. (#11790)
 * Allow configuring a maximum file size as well as a list of allowed content types for avatars. (#11846)
 
+[1.38.6]
+* Update Synapse to 1.53.0
+* [Full changelog](https://github.com/matrix-org/synapse/releases/tag/v1.53.0)
+* Add experimental support for sending to-device messages to application services, as specified by MSC2409. (#11215, #11966)
+* Add a background database update to purge account data for deactivated users. (#11655)
+* Experimental support for MSC3666: including bundled aggregations in server side search results. (#11837)
+* Enable cache time-based expiry by default. The expiry_time config flag has been superseded by expire_caches and cache_entry_ttl. (#11849)
+* Add a callback to allow modules to allow or forbid a 3PID (email address, phone number) from being associated to a local account. (#11854)
+* Stabilize support and remove unstable endpoints for MSC3231. Clients must switch to the stable identifier and endpoint. See the upgrade notes for more information. (#11867)
+* Allow modules to retrieve the current instance's server name and worker name. (#11868)
+* Use a dedicated configurable rate limiter for 3PID invites. (#11892)
+* Support the stable API endpoint for MSC3283: new settings in /capabilities endpoint. (#11933, #11989)
+* Support the dir parameter on the /relations endpoint, per MSC3715. (#11941)
+* Experimental implementation of MSC3706: extensions to /send_join to support reduced response size. (#11967)
+
diff --git a/CloudronManifest.json b/CloudronManifest.json
index 46ba1d2..8976ffb 100644
--- a/CloudronManifest.json
+++ b/CloudronManifest.json
@@ -5,7 +5,7 @@
   "description": "file://DESCRIPTION.md",
   "changelog": "file://CHANGELOG",
   "tagline": "Secure & decentralized communication",
-  "version": "1.38.5",
+  "version": "1.38.6",
   "healthCheckPath": "/",
   "httpPort": 8008,
   "memoryLimit": 536870912,
diff --git a/DESCRIPTION.md b/DESCRIPTION.md
index a6cbbdf..579efec 100644
--- a/DESCRIPTION.md
+++ b/DESCRIPTION.md
@@ -1,4 +1,4 @@
-This app packages Synapse <upstream>1.52.0</upstream>.
+This app packages Synapse <upstream>1.53.0</upstream>.
 
 **This package only provides the Matrix backend. A variety of clients are available
 [here](https://matrix.org/clients/). Riot is a popular web frontend for Matrix and
diff --git a/Dockerfile b/Dockerfile
index 5cf99d9..954736d 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -9,7 +9,7 @@ RUN virtualenv -p python3 /app/code/env
 ENV VIRTUAL_ENV=/app/code/env
 ENV PATH="$VIRTUAL_ENV/bin:$PATH"
 
-ARG VERSION=v1.52.0
+ARG VERSION=v1.53.0
 
 # Synapse (https://github.com/matrix-org/synapse/blob/master/INSTALL.md)
 # lxml - required for previews