diff --git a/roles/matrix-bridge-appservice-slack/tasks/init.yml b/roles/matrix-bridge-appservice-slack/tasks/init.yml
index 2ff7c9420..8cbc71821 100644
--- a/roles/matrix-bridge-appservice-slack/tasks/init.yml
+++ b/roles/matrix-bridge-appservice-slack/tasks/init.yml
@@ -84,4 +84,4 @@
       Please make sure that you're proxying the `{{ something }}`
       URL endpoint to the matrix-appservice-slack container.
       You can expose the container's port using the `matrix_appservice_slack_container_http_host_bind_port` variable.
-  when: "matrix_appservice_slack_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_appservice_slack_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-appservice-webhooks/tasks/init.yml b/roles/matrix-bridge-appservice-webhooks/tasks/init.yml
index 35d62ded2..b888c51f1 100644
--- a/roles/matrix-bridge-appservice-webhooks/tasks/init.yml
+++ b/roles/matrix-bridge-appservice-webhooks/tasks/init.yml
@@ -79,4 +79,4 @@
       Please make sure that you're proxying the `{{ matrix_appservice_webhooks_public_endpoint }}`
       URL endpoint to the matrix-appservice-webhooks container.
       You can expose the container's port using the `matrix_appservice_webhooks_container_http_host_bind_port` variable.
-  when: "matrix_appservice_webhooks_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_appservice_webhooks_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-hookshot/tasks/init.yml b/roles/matrix-bridge-hookshot/tasks/init.yml
index 25204f044..a0f9df978 100644
--- a/roles/matrix-bridge-hookshot/tasks/init.yml
+++ b/roles/matrix-bridge-hookshot/tasks/init.yml
@@ -127,4 +127,4 @@
       Please make sure that you're proxying the `{{ matrix_hookshot_public_endpoint }}`
       URL endpoint to the matrix-hookshot container.
       You can expose the container's ports using the `matrix_hookshot_container_http_host_bind_ports` variable.
-  when: "matrix_hookshot_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_hookshot_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-mautrix-googlechat/tasks/init.yml b/roles/matrix-bridge-mautrix-googlechat/tasks/init.yml
index e64cb44ca..f458df1bf 100644
--- a/roles/matrix-bridge-mautrix-googlechat/tasks/init.yml
+++ b/roles/matrix-bridge-mautrix-googlechat/tasks/init.yml
@@ -67,4 +67,4 @@
       Please make sure that you're proxying the `{{ matrix_mautrix_googlechat_public_endpoint }}`
       URL endpoint to the matrix-mautrix-googlechat container.
       You can expose the container's port using the `matrix_mautrix_googlechat_container_http_host_bind_port` variable.
-  when: "matrix_mautrix_googlechat_enabled|bool and (matrix_nginx_proxy_enabled is not defined or matrix_nginx_proxy_enabled|bool == false)"
+  when: "matrix_mautrix_googlechat_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-mautrix-hangouts/tasks/init.yml b/roles/matrix-bridge-mautrix-hangouts/tasks/init.yml
index 65d4776e2..680dcd88b 100644
--- a/roles/matrix-bridge-mautrix-hangouts/tasks/init.yml
+++ b/roles/matrix-bridge-mautrix-hangouts/tasks/init.yml
@@ -67,4 +67,4 @@
       Please make sure that you're proxying the `{{ matrix_mautrix_hangouts_public_endpoint }}`
       URL endpoint to the matrix-mautrix-hangouts container.
       You can expose the container's port using the `matrix_mautrix_hangouts_container_http_host_bind_port` variable.
-  when: "matrix_mautrix_hangouts_enabled|bool and (matrix_nginx_proxy_enabled is not defined or matrix_nginx_proxy_enabled|bool == false)"
+  when: "matrix_mautrix_hangouts_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-mautrix-telegram/tasks/init.yml b/roles/matrix-bridge-mautrix-telegram/tasks/init.yml
index 267658ef9..764d403d9 100644
--- a/roles/matrix-bridge-mautrix-telegram/tasks/init.yml
+++ b/roles/matrix-bridge-mautrix-telegram/tasks/init.yml
@@ -68,4 +68,4 @@
       Please make sure that you're proxying the `{{ matrix_mautrix_telegram_public_endpoint }}`
       URL endpoint to the matrix-mautrix-telegram container.
       You can expose the container's port using the `matrix_mautrix_telegram_container_http_host_bind_port` variable.
-  when: "matrix_mautrix_telegram_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_mautrix_telegram_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-mx-puppet-slack/tasks/init.yml b/roles/matrix-bridge-mx-puppet-slack/tasks/init.yml
index 897f3f8fe..66d51784e 100644
--- a/roles/matrix-bridge-mx-puppet-slack/tasks/init.yml
+++ b/roles/matrix-bridge-mx-puppet-slack/tasks/init.yml
@@ -68,4 +68,4 @@
       Please make sure that you're proxying the `{{ matrix_mx_puppet_slack_redirect_path }}`
       URL endpoint to the matrix-mx-puppet-slack container.
       You can expose the container's port using the `matrix_appservice_slack_container_http_host_bind_port` variable.
-  when: "matrix_mx_puppet_slack_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_mx_puppet_slack_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-bridge-mx-puppet-twitter/tasks/init.yml b/roles/matrix-bridge-mx-puppet-twitter/tasks/init.yml
index 9d868bfea..757f1f414 100644
--- a/roles/matrix-bridge-mx-puppet-twitter/tasks/init.yml
+++ b/roles/matrix-bridge-mx-puppet-twitter/tasks/init.yml
@@ -68,4 +68,4 @@
       Please make sure that you're proxying the `{{ matrix_mx_puppet_twitter_redirect_path }}`
       URL endpoint to the matrix-mx-puppet-twitter container.
       You can expose the container's port using the `matrix_mx_puppet_twitter_container_http_host_bind_port` variable.
-  when: "matrix_mx_puppet_twitter_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_mx_puppet_twitter_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-etherpad/tasks/init.yml b/roles/matrix-etherpad/tasks/init.yml
index b155064cf..392addd04 100644
--- a/roles/matrix-etherpad/tasks/init.yml
+++ b/roles/matrix-etherpad/tasks/init.yml
@@ -61,4 +61,4 @@
       Please make sure that you're proxying the `{{ matrix_etherpad_public_endpoint }}`
       URL endpoint to the matrix-etherpad container.
       You can expose the container's port using the `matrix_etherpad_container_http_host_bind_port` variable.
-  when: "matrix_etherpad_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_etherpad_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-registration/tasks/init.yml b/roles/matrix-registration/tasks/init.yml
index cae182587..44a887d18 100644
--- a/roles/matrix-registration/tasks/init.yml
+++ b/roles/matrix-registration/tasks/init.yml
@@ -66,4 +66,4 @@
       Please make sure that you're proxying the `{{ matrix_registration_public_endpoint }}`
       URL endpoint to the matrix-registration container.
       You can expose the container's port using the `matrix_registration_container_http_host_bind_port` variable.
-  when: "matrix_registration_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_registration_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"
diff --git a/roles/matrix-synapse-admin/tasks/init.yml b/roles/matrix-synapse-admin/tasks/init.yml
index ccaa03f60..de8c00466 100644
--- a/roles/matrix-synapse-admin/tasks/init.yml
+++ b/roles/matrix-synapse-admin/tasks/init.yml
@@ -57,4 +57,4 @@
       Please make sure that you're proxying the `{{ matrix_synapse_admin_public_endpoint }}`
       URL endpoint to the matrix-synapse-admin container.
       You can expose the container's port using the `matrix_synapse_admin_container_http_host_bind_port` variable.
-  when: "matrix_synapse_admin_enabled|bool and matrix_nginx_proxy_enabled is not defined"
+  when: "matrix_synapse_admin_enabled|bool and not matrix_nginx_proxy_enabled|default(False)|bool"