diff --git a/caddy-update.sh b/caddy-update.sh
new file mode 100755
index 0000000..424ad0e
--- /dev/null
+++ b/caddy-update.sh
@@ -0,0 +1,2 @@
+#!/usr/bin/env bash
+ansible-playbook -i inventories/hetzner playbooks/05-update-caddy.yml
diff --git a/playbooks/init_hetzer_vm.yaml b/playbooks/00-init_hetzer_vm.yaml
similarity index 100%
rename from playbooks/init_hetzer_vm.yaml
rename to playbooks/00-init_hetzer_vm.yaml
diff --git a/playbooks/everything.yaml b/playbooks/01-everything.yaml
similarity index 91%
rename from playbooks/everything.yaml
rename to playbooks/01-everything.yaml
index b76789b..7f53c6d 100644
--- a/playbooks/everything.yaml
+++ b/playbooks/01-everything.yaml
@@ -1,5 +1,5 @@
 - name: Run maintenance playbook
-  ansible.builtin.import_playbook: maintenance.yaml
+  ansible.builtin.import_playbook: 02-maintenance.yaml
 
 - name: Ensure Docker for Docker_Hosts
   hosts: Docker_Hosts
diff --git a/playbooks/maintenance.yaml b/playbooks/02-maintenance.yaml
similarity index 100%
rename from playbooks/maintenance.yaml
rename to playbooks/02-maintenance.yaml
diff --git a/playbooks/docker-compose.yml b/playbooks/04-compose-up.yml
similarity index 100%
rename from playbooks/docker-compose.yml
rename to playbooks/04-compose-up.yml
diff --git a/playbooks/05-update-caddy.yml b/playbooks/05-update-caddy.yml
new file mode 100644
index 0000000..380b61c
--- /dev/null
+++ b/playbooks/05-update-caddy.yml
@@ -0,0 +1,28 @@
+- name: Update Caddyfile and reload Caddy
+  hosts: cit-docker-host
+  tasks:
+    - name: Deploy desired projects, adding new ones and updating existing ones
+      ansible.posix.synchronize:
+        src: "../docker_compose_applications/reverse-proxy/Caddyfile"
+        dest: "/ansible_docker_compose/projects/reverse-proxy/Caddyfile"
+        mode: push
+        archive: false
+        copy_links: false
+        delete: true
+        dirs: false
+        existing_only: false
+        recursive: true
+        owner: false
+        group: false
+        perms: true
+        links: true
+        times: false
+        verify_host: true
+      become: true
+
+    - name: Restart Caddy container
+      community.docker.docker_container:
+        name: caddy
+        state: started
+        restart: yes
+      become: true
diff --git a/playbooks/roles/authorized_keys/files/cit_authorized_keys b/playbooks/roles/authorized_keys/files/cit_authorized_keys
index 7718f26..44e7720 100644
--- a/playbooks/roles/authorized_keys/files/cit_authorized_keys
+++ b/playbooks/roles/authorized_keys/files/cit_authorized_keys
@@ -1,2 +1 @@
 ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIJsmbhT8iopyZ83la/mFZf8eUDYAwCJtsWGaGybb1fNp
-