diff --git a/roles/sys-dns-hetzner-rdns/tasks/main.yml b/roles/sys-dns-hetzner-rdns/tasks/main.yml
index 6774ff9d..e2e87593 100644
--- a/roles/sys-dns-hetzner-rdns/tasks/main.yml
+++ b/roles/sys-dns-hetzner-rdns/tasks/main.yml
@@ -14,11 +14,11 @@
 - name: "Note: both Cloud token and Robot creds provided; using Cloud flavor"
   debug:
     msg: "Both HETZNER_API_TOKEN and Robot credentials present → proceeding with Cloud (hcloud) flavor."
-  when: _use_cloud and _use_robot
+  when: _use_cloud | bool and _use_robot | bool
 
 - name: Include Cloud flavor (hcloud)
   include_tasks: flavors/cloud.yml
-  when: _use_cloud
+  when: _use_cloud | bool
 
 - name: Include Robot flavor (Robot Webservice)
   include_tasks: flavors/robot.yml
diff --git a/roles/sys-front-inj-css/tasks/main.yml b/roles/sys-front-inj-css/tasks/main.yml
index f57fcc38..9096d947 100644
--- a/roles/sys-front-inj-css/tasks/main.yml
+++ b/roles/sys-front-inj-css/tasks/main.yml
@@ -14,7 +14,7 @@
     app_style_present: "{{ _app_style_src | length > 0 }}"
 
 - name: "Deploy per-app '{{ app_style_src }}' to '{{ css_app_dst }}'"
-  when: app_style_present
+  when: app_style_present | bool
   copy:
     content:  "{{ lookup('template', app_style_src) }}"
     dest:     "{{ css_app_dst }}"
diff --git a/roles/web-app-gitea/tasks/main.yml b/roles/web-app-gitea/tasks/main.yml
index d5dd267e..1b87aa52 100644
--- a/roles/web-app-gitea/tasks/main.yml
+++ b/roles/web-app-gitea/tasks/main.yml
@@ -56,7 +56,7 @@
 
 - name: Execute Cleanup Routines
   include_tasks: 03_cleanup.yml 
-  when: MODE_CLEANUP
+  when: MODE_CLEANUP | bool
 
 - name: Include DNS role to register Gitea domain(s)
   include_role:
diff --git a/roles/web-app-nextcloud/tasks/main.yml b/roles/web-app-nextcloud/tasks/main.yml
index a0d30401..eaf56301 100644
--- a/roles/web-app-nextcloud/tasks/main.yml
+++ b/roles/web-app-nextcloud/tasks/main.yml
@@ -36,4 +36,4 @@
   vars:
     plugin_key:   "{{ plugin_item.key }}"
     plugin_value: "{{ plugin_item.value }}"
-  when: NEXTCLOUD_PLUGINS_ENABLED
+  when: NEXTCLOUD_PLUGINS_ENABLED | bool
diff --git a/roles/web-app-wordpress/tasks/main.yml b/roles/web-app-wordpress/tasks/main.yml
index 0037f45a..59ce31e2 100644
--- a/roles/web-app-wordpress/tasks/main.yml
+++ b/roles/web-app-wordpress/tasks/main.yml
@@ -56,7 +56,7 @@
         plugin_name: "{{ item.key }}"
         plugin_enabled: "{{ item.value.enabled | bool }}"
         plugin_task_path: "{{ [role_path, 'tasks/plugins', plugin_name  ~ '.yml' ] | path_join }}"
-      when: plugin_enabled
+      when: plugin_enabled | bool
 
 - name: Detect if WordPress is Multisite
   command: >