diff --git a/roles/authentik/tasks/main.yml b/roles/authentik/tasks/main.yml
index 1471836..1947fc4 100644
--- a/roles/authentik/tasks/main.yml
+++ b/roles/authentik/tasks/main.yml
@@ -49,22 +49,32 @@
   until: blueprint_wait_result.rc == 0
   when: blueprints_changed
 
-- name: Render LDAP outpost token script
+# Pin known tokens on the LDAP outpost and on any proxy outpost that
+# declares one, so co-located outposts (e.g. a proxy outpost on another
+# host) can authenticate against the authentik server with the token from
+# the vault instead of the auto-generated one the blueprint creates.
+- name: Set fact whether any outpost needs a pinned token
+  ansible.builtin.set_fact:
+    _authentik_outpost_tokens: >-
+      {{ (authentik_ldap_outpost.name is defined)
+         or (authentik_proxy_outposts | default([]) | selectattr('token', 'defined') | list | length > 0) }}
+
+- name: Render outpost token script
   template:
     src: set-outpost-token.py.j2
     dest: "{{ authentik_docker_volume_dir }}/data/set-outpost-token.py"
     mode: '0644'
-  when: authentik_ldap_outpost.name is defined
-  register: ldap_token_script
+  when: _authentik_outpost_tokens | bool
+  register: outpost_token_script
 
-- name: Set known token for LDAP outpost
+- name: Set known tokens for outposts
   community.docker.docker_compose_v2_exec:
     project_src: "{{ authentik_docker_compose_dir }}"
     service: server
     command: ak shell -c "exec(open('/data/set-outpost-token.py').read())"
-  register: ldap_token_result
-  changed_when: "'changed' in ldap_token_result.stdout"
+  register: outpost_token_result
+  changed_when: "'changed' in outpost_token_result.stdout"
   retries: 30
   delay: 10
-  until: ldap_token_result.rc == 0
-  when: authentik_ldap_outpost.name is defined and (blueprints_changed or ldap_token_script.changed)
\ No newline at end of file
+  until: outpost_token_result.rc == 0
+  when: (_authentik_outpost_tokens | bool) and (blueprints_changed or outpost_token_script.changed)
\ No newline at end of file
diff --git a/roles/authentik/templates/docker-compose.yml.j2 b/roles/authentik/templates/docker-compose.yml.j2
index cd3ef1e..ce427f2 100644
--- a/roles/authentik/templates/docker-compose.yml.j2
+++ b/roles/authentik/templates/docker-compose.yml.j2
@@ -23,7 +23,9 @@ services:
     command: server
     healthcheck:
       test: ["CMD", "ak", "healthcheck"]
-      start_period: 30s
+      # Cold first boot runs DB migrations + app init (~90s observed);
+      # start_period must cover that or compose --wait trips unhealthy.
+      start_period: 120s
       interval: 10s
       retries: 5
       timeout: 5s
diff --git a/roles/authentik/templates/set-outpost-token.py.j2 b/roles/authentik/templates/set-outpost-token.py.j2
index 0b61705..ffaa56b 100644
--- a/roles/authentik/templates/set-outpost-token.py.j2
+++ b/roles/authentik/templates/set-outpost-token.py.j2
@@ -1,10 +1,26 @@
 from authentik.outposts.models import Outpost
 from authentik.core.models import Token
-o = Outpost.objects.get(name='{{ authentik_ldap_outpost.name }}')
-t = Token.objects.get(identifier=o.token_identifier)
-if t.key != '{{ authentik_ldap_outpost.token }}':
-    t.key = '{{ authentik_ldap_outpost.token }}'
-    t.save(update_fields=['key'])
-    print('changed')
-else:
-    print('ok')
+
+# (outpost name, desired token key) for every outpost we pin a known
+# token on: the LDAP outpost plus any proxy outpost that declares a
+# `token` (co-located proxy outposts authenticate with it against the
+# authentik server).
+_targets = [
+{% if authentik_ldap_outpost.name is defined %}
+    ('{{ authentik_ldap_outpost.name }}', '{{ authentik_ldap_outpost.token }}'),
+{% endif %}
+{% for o in authentik_proxy_outposts | default([]) if o.token is defined %}
+    ('{{ o.name }}', '{{ o.token }}'),
+{% endfor %}
+]
+
+changed = False
+for name, key in _targets:
+    o = Outpost.objects.get(name=name)
+    t = Token.objects.get(identifier=o.token_identifier)
+    if t.key != key:
+        t.key = key
+        t.save(update_fields=['key'])
+        changed = True
+
+print('changed' if changed else 'ok')