diff --git a/roles/matrix-synapse/defaults/main.yml b/roles/matrix-synapse/defaults/main.yml
index 075e7dd0..460483e0 100644
--- a/roles/matrix-synapse/defaults/main.yml
+++ b/roles/matrix-synapse/defaults/main.yml
@@ -15,8 +15,8 @@ matrix_synapse_docker_image_name_prefix: "{{ 'localhost/' if matrix_synapse_cont
 # amd64 gets released first.
 # arm32 relies on self-building, so the same version can be built immediately.
 # arm64 users need to wait for a prebuilt image to become available.
-matrix_synapse_version: v1.43.0
-matrix_synapse_version_arm64: v1.43.0
+matrix_synapse_version: v1.44.0
+matrix_synapse_version_arm64: v1.44.0
 matrix_synapse_docker_image_tag: "{{ matrix_synapse_version if matrix_architecture in ['arm32', 'amd64'] else matrix_synapse_version_arm64 }}"
 matrix_synapse_docker_image_force_pull: "{{ matrix_synapse_docker_image.endswith(':latest') }}"
 
diff --git a/roles/matrix-synapse/templates/synapse/homeserver.yaml.j2 b/roles/matrix-synapse/templates/synapse/homeserver.yaml.j2
index 2fb08e0a..9e558632 100644
--- a/roles/matrix-synapse/templates/synapse/homeserver.yaml.j2
+++ b/roles/matrix-synapse/templates/synapse/homeserver.yaml.j2
@@ -2612,12 +2612,16 @@ user_directory:
     #enabled: false
 
     # Defines whether to search all users visible to your HS when searching
-    # the user directory, rather than limiting to users visible in public
-    # rooms. Defaults to false.
+    # the user directory. If false, search results will only contain users
+    # visible in public rooms and users sharing a room with the requester.
+    # Defaults to false.
     #
-    # 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
+    # NB. If you set this to true, and the last time the user_directory search
+    # indexes were (re)built was before Synapse 1.44, you'll have to
+    # rebuild the indexes in order to search through all known users.
+    # These indexes are built the first time Synapse starts; admins can
+    # manually trigger a rebuild following the instructions at
+    #     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.