diff --git a/roles/custom/matrix-authentication-service/tasks/mas_cli_syn2mas.yml b/roles/custom/matrix-authentication-service/tasks/mas_cli_syn2mas.yml
index 90cb9ab74..b058d87d8 100644
--- a/roles/custom/matrix-authentication-service/tasks/mas_cli_syn2mas.yml
+++ b/roles/custom/matrix-authentication-service/tasks/mas_cli_syn2mas.yml
@@ -19,7 +19,7 @@
   ansible.builtin.fail:
     msg: >-
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_authentication_service_syn2mas_synapse_homeserver_config_path', when: true}
 
diff --git a/roles/custom/matrix-authentication-service/tasks/validate_config.yml b/roles/custom/matrix-authentication-service/tasks/validate_config.yml
index 675e0a13f..ee40118a5 100644
--- a/roles/custom/matrix-authentication-service/tasks/validate_config.yml
+++ b/roles/custom/matrix-authentication-service/tasks/validate_config.yml
@@ -9,7 +9,7 @@
   ansible.builtin.fail:
     msg: >-
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_authentication_service_hostname', when: true}
     - {'name': 'matrix_authentication_service_config_database_username', when: true}
diff --git a/roles/custom/matrix-element-call/tasks/validate_config.yml b/roles/custom/matrix-element-call/tasks/validate_config.yml
index 738b2de3c..fcc4f4bb8 100644
--- a/roles/custom/matrix-element-call/tasks/validate_config.yml
+++ b/roles/custom/matrix-element-call/tasks/validate_config.yml
@@ -17,7 +17,7 @@
   ansible.builtin.fail:
     msg: >
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_element_call_container_network', when: true}
     - {'name': 'matrix_element_call_hostname', when: true}
diff --git a/roles/custom/matrix-livekit-jwt-service/tasks/validate_config.yml b/roles/custom/matrix-livekit-jwt-service/tasks/validate_config.yml
index f731898f2..440f720fd 100644
--- a/roles/custom/matrix-livekit-jwt-service/tasks/validate_config.yml
+++ b/roles/custom/matrix-livekit-jwt-service/tasks/validate_config.yml
@@ -10,7 +10,7 @@
   ansible.builtin.fail:
     msg: >
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_livekit_jwt_service_hostname', when: true}
     - {'name': 'matrix_livekit_jwt_service_container_network', when: true}
diff --git a/roles/custom/matrix-static-files/tasks/validate_config.yml b/roles/custom/matrix-static-files/tasks/validate_config.yml
index 2697fa654..fb2319ca3 100644
--- a/roles/custom/matrix-static-files/tasks/validate_config.yml
+++ b/roles/custom/matrix-static-files/tasks/validate_config.yml
@@ -8,7 +8,7 @@
   ansible.builtin.fail:
     msg: >-
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_hostname', when: "{{ matrix_static_files_container_labels_well_known_matrix_endpoint_enabled }}"}
     - {'name': 'matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_path_prefix', when: "{{ matrix_static_files_container_labels_well_known_matrix_endpoint_enabled }}"}
diff --git a/roles/custom/matrix-synapse/tasks/validate_config.yml b/roles/custom/matrix-synapse/tasks/validate_config.yml
index 47156c801..c261f5c4e 100644
--- a/roles/custom/matrix-synapse/tasks/validate_config.yml
+++ b/roles/custom/matrix-synapse/tasks/validate_config.yml
@@ -10,7 +10,7 @@
   ansible.builtin.fail:
     msg: >-
       You need to define a required configuration setting (`{{ item.name }}`).
-  when: "item.when | bool and vars[item.name] | length == 0"
+  when: "item.when | bool and vars[item.name] | string | length == 0"
   with_items:
     - {'name': 'matrix_synapse_username', when: true}
     - {'name': 'matrix_synapse_uid', when: true}