diff --git a/roles/matrix-bridge-mautrix-facebook/tasks/setup_install.yml b/roles/matrix-bridge-mautrix-facebook/tasks/setup_install.yml
index 5a70c2e4..2656c5ae 100644
--- a/roles/matrix-bridge-mautrix-facebook/tasks/setup_install.yml
+++ b/roles/matrix-bridge-mautrix-facebook/tasks/setup_install.yml
@@ -18,16 +18,17 @@
 
 - name: Ensure Mautrix Facebook paths exist
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - "{{ matrix_mautrix_facebook_base_path }}"
-    - "{{ matrix_mautrix_facebook_config_path }}"
-    - "{{ matrix_mautrix_facebook_data_path }}"
-    - { src: "{{ matrix_mautrix_facebook_docker_src_files_path }}", when: "{{ matrix_mautrix_facebook_container_image_self_build }}" }
+    - { path: "{{ matrix_mautrix_facebook_base_path }}", when: true }
+    - { path: "{{ matrix_mautrix_facebook_config_path }}", when: true }
+    - { path: "{{ matrix_mautrix_facebook_data_path }}", when: true }
+    - { path: "{{ matrix_mautrix_facebook_docker_src_files_path }}", when: "{{ matrix_mautrix_facebook_container_image_self_build }}" }
+  when: item.when|bool
 
 - name: Ensure Mautrix Facebook repository is present on self-build
   git:
diff --git a/roles/matrix-bridge-mautrix-hangouts/tasks/setup_install.yml b/roles/matrix-bridge-mautrix-hangouts/tasks/setup_install.yml
index db1fe736..a30367f3 100644
--- a/roles/matrix-bridge-mautrix-hangouts/tasks/setup_install.yml
+++ b/roles/matrix-bridge-mautrix-hangouts/tasks/setup_install.yml
@@ -18,18 +18,17 @@
 
 - name: Ensure Mautrix Hangouts paths exist
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - "{{ matrix_mautrix_hangouts_base_path }}"
-    - "{{ matrix_mautrix_hangouts_config_path }}"
-    - "{{ matrix_mautrix_hangouts_data_path }}"
-    - { src: "{{ matrix_mautrix_hangouts_docker_src_files_path }}", when: "{{ matrix_mautrix_hangouts_container_image_self_build }}" }
-
-  when: matrix_mautrix_hangouts_enabled|bool and not matrix_mautrix_hangouts_container_image_self_build
+    - { path: "{{ matrix_mautrix_hangouts_base_path }}", when: true }
+    - { path: "{{ matrix_mautrix_hangouts_config_path }}", when: true }
+    - { path: "{{ matrix_mautrix_hangouts_data_path }}", when: true }
+    - { path: "{{ matrix_mautrix_hangouts_docker_src_files_path }}", when: "{{ matrix_mautrix_hangouts_container_image_self_build }}" }
+  when: matrix_mautrix_hangouts_enabled|bool and item.when|bool
 
 - name: Ensure Mautrix Hangots repository is present on self build
   git:
diff --git a/roles/matrix-coturn/tasks/setup_coturn.yml b/roles/matrix-coturn/tasks/setup_coturn.yml
index d86e4b22..479e6044 100644
--- a/roles/matrix-coturn/tasks/setup_coturn.yml
+++ b/roles/matrix-coturn/tasks/setup_coturn.yml
@@ -6,14 +6,14 @@
 
 - name: Ensure Matrix Coturn path exists
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - { src: "{{ matrix_coturn_docker_src_files_path }}", when: "{{ matrix_coturn_container_image_self_build }}"}
-  when: matrix_riot_web_enabled|bool
+    - { path: "{{ matrix_coturn_docker_src_files_path }}", when: "{{ matrix_coturn_container_image_self_build }}"}
+  when: matrix_riot_web_enabled|bool and item.when
 
 - name: Ensure Coturn image is pulled
   docker_image:
diff --git a/roles/matrix-mxisd/tasks/setup_mxisd.yml b/roles/matrix-mxisd/tasks/setup_mxisd.yml
index 27c00c70..aa780119 100644
--- a/roles/matrix-mxisd/tasks/setup_mxisd.yml
+++ b/roles/matrix-mxisd/tasks/setup_mxisd.yml
@@ -6,16 +6,16 @@
 
 - name: Ensure mxisd paths exist
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - "{{ matrix_mxisd_config_path }}"
-    - "{{ matrix_mxisd_data_path }}"
-    - { src: "{{ matrix_mxisd_docker_src_files_path }}", when: "{{ matrix_mxisd_container_image_self_build }}"}
-  when: matrix_mxisd_enabled|bool
+    - { path: "{{ matrix_mxisd_config_path }}", when: true }
+    - { path: "{{ matrix_mxisd_data_path }}", when: true }
+    - { path: "{{ matrix_mxisd_docker_src_files_path }}", when: "{{ matrix_mxisd_container_image_self_build }}"}
+  when: matrix_mxisd_enabled|bool and item.when
 
 - name: Ensure mxisd image is pulled
   docker_image:
diff --git a/roles/matrix-riot-web/tasks/setup_riot_web.yml b/roles/matrix-riot-web/tasks/setup_riot_web.yml
index feccbe81..e78da350 100644
--- a/roles/matrix-riot-web/tasks/setup_riot_web.yml
+++ b/roles/matrix-riot-web/tasks/setup_riot_web.yml
@@ -6,15 +6,15 @@
 
 - name: Ensure Matrix riot-web path exists
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - "{{ matrix_riot_web_data_path }}"
-    - { src: "{{ matrix_riot_web_docker_src_files_path }}", when: "{{ matrix_riot_web_container_image_self_build }}" }
-  when: matrix_riot_web_enabled|bool
+    - { path: "{{ matrix_riot_web_data_path }}", when: true }
+    - { path: "{{ matrix_riot_web_docker_src_files_path }}", when: "{{ matrix_riot_web_container_image_self_build }}" }
+  when: matrix_riot_web_enabled|bool and item.when
 
 - name: Ensure riot-web Docker image is pulled
   docker_image:
diff --git a/roles/matrix-synapse/tasks/setup_synapse.yml b/roles/matrix-synapse/tasks/setup_synapse.yml
index 8d5f72d2..c40ae170 100644
--- a/roles/matrix-synapse/tasks/setup_synapse.yml
+++ b/roles/matrix-synapse/tasks/setup_synapse.yml
@@ -2,20 +2,20 @@
 
 - name: Ensure Synapse paths exist
   file:
-    path: "{{ item }}"
+    path: "{{ item.path }}"
     state: directory
     mode: 0750
     owner: "{{ matrix_user_username }}"
     group: "{{ matrix_user_username }}"
   with_items:
-    - "{{ matrix_synapse_config_dir_path }}"
-    - "{{ matrix_synapse_run_path }}"
-    - "{{ matrix_synapse_ext_path }}"
-    - { src: "{{ matrix_synapse_docker_src_files_path }}", when: "{{ matrix_synapse_container_image_self_build }}" }
+    - { path: "{{ matrix_synapse_config_dir_path }}", when: true }
+    - { path: "{{ matrix_synapse_run_path }}", when: true }
+    - { path: "{{ matrix_synapse_ext_path }}", when: true }
+    - { path: "{{ matrix_synapse_docker_src_files_path }}", when: "{{ matrix_synapse_container_image_self_build }}" }
     # We handle matrix_synapse_media_store_path elsewhere (in ./synapse/setup_install.yml),
     # because if it's using Goofys and it's already mounted (from before),
     # trying to chown/chmod it here will cause trouble.
-  when: "matrix_synapse_enabled|bool or matrix_s3_media_store_enabled|bool"
+  when: "(matrix_synapse_enabled|bool or matrix_s3_media_store_enabled|bool) and item.when"
 
 - import_tasks: "{{ role_path }}/tasks/ext/setup.yml"