diff --git a/roles/matrix-nginx-proxy/defaults/main.yml b/roles/matrix-nginx-proxy/defaults/main.yml
index 79211a233..88ebd7cd1 100644
--- a/roles/matrix-nginx-proxy/defaults/main.yml
+++ b/roles/matrix-nginx-proxy/defaults/main.yml
@@ -183,6 +183,10 @@ matrix_nginx_proxy_proxy_matrix_identity_api_addr_sans_container: "127.0.0.1:809
 # Controls whether proxying for metrics (`/_synapse/metrics`) should be done (on the matrix domain)
 matrix_nginx_proxy_proxy_synapse_metrics: false
 matrix_nginx_proxy_proxy_synapse_metrics_basic_auth_enabled: false
+# The following value will be written verbatim to the htpasswd file that stores the password for nginx to check against and needs to be encoded appropriately.
+# Read the manpage at `man 1 htpasswd` to learn more, then encrypt your password, and paste the encrypted value here.
+# e.g. `htpasswd -c mypass.htpasswd prometheus` and enter `mysecurepw` when prompted yields `prometheus:$apr1$wZhqsn.U$7LC3kMmjUbjNAZjyMyvYv/`
+# The part after `prometheus:` is needed here. matrix_nginx_proxy_proxy_synapse_metrics_basic_auth_key: "$apr1$wZhqsn.U$7LC3kMmjUbjNAZjyMyvYv/"
 matrix_nginx_proxy_proxy_synapse_metrics_basic_auth_key: ""
 
 # The addresses where the Matrix Client API is.
@@ -432,7 +436,7 @@ matrix_ssl_additional_domains_to_obtain_certificates_for: []
 
 # Controls whether to obtain production or staging certificates from Let's Encrypt.
 matrix_ssl_lets_encrypt_staging: false
-matrix_ssl_lets_encrypt_certbot_docker_image: "{{ matrix_container_global_registry_prefix }}certbot/certbot:{{ matrix_ssl_architecture }}-v1.19.0"
+matrix_ssl_lets_encrypt_certbot_docker_image: "{{ matrix_container_global_registry_prefix }}certbot/certbot:{{ matrix_ssl_architecture }}-v1.20.0"
 matrix_ssl_lets_encrypt_certbot_docker_image_force_pull: "{{ matrix_ssl_lets_encrypt_certbot_docker_image.endswith(':latest') }}"
 matrix_ssl_lets_encrypt_certbot_standalone_http_port: 2402
 matrix_ssl_lets_encrypt_support_email: ~
diff --git a/roles/matrix-synapse/defaults/main.yml b/roles/matrix-synapse/defaults/main.yml
index 075e7dd0c..460483e07 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 2fb08e0ae..9e5586321 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.