diff --git a/roles/custom/matrix-synapse/defaults/main.yml b/roles/custom/matrix-synapse/defaults/main.yml
index 4866f2b6d..aac120c3c 100644
--- a/roles/custom/matrix-synapse/defaults/main.yml
+++ b/roles/custom/matrix-synapse/defaults/main.yml
@@ -358,13 +358,37 @@ matrix_synapse_goofys_systemd_required_services_list_default: "{{ [devture_syste
 matrix_synapse_goofys_systemd_required_services_list_auto: []
 matrix_synapse_goofys_systemd_required_services_list_custom: []
 
-# Controls how long to sleep for after starting the matrix-synapse container.
-#
-# Delaying, so that the homeserver can manage to fully start and various services
-# that depend on it (`matrix_synapse_systemd_required_services_list` and `matrix_synapse_systemd_wanted_services_list`)
-# may only start after the homeserver is up and running.
-#
-# This can be set to 0 to remove the delay.
+# Controls the post-start health check in the systemd service.
+# When enabled, ExecStartPost polls Synapse's /health endpoint via `docker exec` + `curl`,
+# keeping the service in "activating (start-post)" state until Synapse is ready.
+# Services with After=matrix-synapse.service will properly wait.
+matrix_synapse_systemd_healthcheck_enabled: true
+matrix_synapse_systemd_healthcheck_max_retries: 60
+matrix_synapse_systemd_healthcheck_interval_seconds: 1
+
+# The command used for the health check in ExecStartPost.
+# Uses `docker exec` + `curl` (available in the Synapse container image) to poll /health.
+# We intentionally don't rely on Docker's built-in container HEALTHCHECK (polling via `docker inspect`),
+# because its check interval (default: 15s) is too slow for our startup needs, and lowering it
+# would add unnecessary overhead for the entire container lifetime. We only need fast polling at startup.
+matrix_synapse_systemd_healthcheck_command: >-
+  {{ devture_systemd_docker_base_host_command_sh }} -c
+  'for i in $(seq 1 {{ matrix_synapse_systemd_healthcheck_max_retries }}); do
+  echo "[Attempt $i/{{ matrix_synapse_systemd_healthcheck_max_retries }}] Synapse systemd health check: checking readiness via /health..";
+  {{ devture_systemd_docker_base_host_command_docker }} exec matrix-synapse
+  curl -fSs http://localhost:8008/health > /dev/null 2>&1 && echo "[Attempt $i/{{ matrix_synapse_systemd_healthcheck_max_retries }}] Synapse systemd health check: passed" && exit 0;
+  echo "[Attempt $i/{{ matrix_synapse_systemd_healthcheck_max_retries }}] Synapse systemd health check: not ready yet, retrying in {{ matrix_synapse_systemd_healthcheck_interval_seconds }}s..";
+  sleep {{ matrix_synapse_systemd_healthcheck_interval_seconds }};
+  done; echo "[Attempt $i/{{ matrix_synapse_systemd_healthcheck_max_retries }}] Synapse systemd health check: failed after {{ matrix_synapse_systemd_healthcheck_max_retries }} attempts"; exit 1'
+
+# Controls how long to sleep for after the systemd health check passes.
+# Even after Synapse is healthy, the reverse proxy (e.g. Traefik) needs time to discover
+# the container and register its routes. Traefik's `providers.providersThrottleDuration`
+# (default: 2s; see https://doc.traefik.io/traefik/providers/overview/#providersthrottleduration)
+# adds a delay before applying new configuration from Docker events, meaning routes
+# typically become available ~2-3 seconds after a container starts.
+# Without this delay, services depending on Synapse may encounter 404 errors
+# when connecting through the reverse proxy.
 matrix_synapse_systemd_service_post_start_delay_seconds: 10
 
 matrix_synapse_in_container_python_packages_path: "/usr/local/lib/python3.13/site-packages"
diff --git a/roles/custom/matrix-synapse/templates/synapse/systemd/matrix-synapse.service.j2 b/roles/custom/matrix-synapse/templates/synapse/systemd/matrix-synapse.service.j2
index 1b28bb85d..31b11697f 100644
--- a/roles/custom/matrix-synapse/templates/synapse/systemd/matrix-synapse.service.j2
+++ b/roles/custom/matrix-synapse/templates/synapse/systemd/matrix-synapse.service.j2
@@ -69,8 +69,12 @@ ExecStartPre={{ devture_systemd_docker_base_host_command_docker }} network conne
 
 ExecStart={{ devture_systemd_docker_base_host_command_docker }} start --attach matrix-synapse
 
+{% if matrix_synapse_systemd_healthcheck_enabled %}
+ExecStartPost={{ matrix_synapse_systemd_healthcheck_command }}
+{% endif %}
+
 {% if matrix_synapse_systemd_service_post_start_delay_seconds > 0 %}
-ExecStartPost=-{{ matrix_host_command_sleep }} {{ matrix_synapse_systemd_service_post_start_delay_seconds }}
+ExecStartPost=-{{ matrix_host_command_sleep }} {{ matrix_synapse_systemd_service_post_start_delay_seconds }}
 {% endif %}
 
 ExecStop=-{{ devture_systemd_docker_base_host_command_sh }} -c '{{ devture_systemd_docker_base_host_command_docker }} stop -t {{ devture_systemd_docker_base_container_stop_grace_time_seconds }} matrix-synapse 2>/dev/null || true'