diff --git a/.woodpecker/deploy-netbird-proxy.yml b/.woodpecker/deploy-netbird-proxy.yml
index ed641379..cbe04532 100644
--- a/.woodpecker/deploy-netbird-proxy.yml
+++ b/.woodpecker/deploy-netbird-proxy.yml
@@ -4,6 +4,9 @@ when:
     branch: master
     path:
       - "ansible/roles/netbird-proxy/**"
+      # install-netbird-proxy.yml also applies the netbird-proxy-watchdog role,
+      # so changes to it must redeploy this host too.
+      - "ansible/roles/netbird-proxy-watchdog/**"
       - "ansible/plays/install-netbird-proxy.yml"
       - ".woodpecker/deploy-netbird-proxy.yml"
   - event: manual
diff --git a/.woodpecker/deploy-netbird-server.yml b/.woodpecker/deploy-netbird-server.yml
index 227d8faa..7b92ca01 100644
--- a/.woodpecker/deploy-netbird-server.yml
+++ b/.woodpecker/deploy-netbird-server.yml
@@ -2,6 +2,9 @@ when:
   - event: push
     path:
       - "ansible/roles/netbird-server/**"
+      # install-netbird-server.yml also applies the netbird-proxy-watchdog role,
+      # so changes to it must redeploy this host too.
+      - "ansible/roles/netbird-proxy-watchdog/**"
       - "ansible/plays/install-netbird-server.yml"
       - ".woodpecker/deploy-netbird-server.yml"
   - event: manual