diff --git a/roles/nginx/templates/nginx.conf.j2 b/roles/nginx/templates/nginx.conf.j2
index 6b60169863..49f5b7f929 100644
--- a/roles/nginx/templates/nginx.conf.j2
+++ b/roles/nginx/templates/nginx.conf.j2
@@ -50,7 +50,22 @@ pid        /run/nginx.pid;
 {% endblock %}
 
 http {
-  {% block http_begin %}{% endblock %}
+  {% block http_begin %}
+  map $upstream_cache_status $header_x_cache_enabled {
+    default true;
+    BYPASS  "";
+  }
+
+  map $server_addr:$remote_addr $is_loopback_request {
+    "~^([^:]+):\1$" 1;
+    default         0;
+  }
+
+  map $is_loopback_request:$header_x_cache_enabled $loopback_header_x_cache_enabled {
+    default "";
+    1:true  true;
+  }
+  {% endblock %}
 
   {% block server_tokens -%}
   # Hide nginx version information.
diff --git a/roles/wordpress-setup/templates/wordpress-site.conf.j2 b/roles/wordpress-setup/templates/wordpress-site.conf.j2
index 95b406439a..72b63fc0a3 100644
--- a/roles/wordpress-setup/templates/wordpress-site.conf.j2
+++ b/roles/wordpress-setup/templates/wordpress-site.conf.j2
@@ -21,6 +21,9 @@ server {
   index index.php index.htm index.html;
   add_header Fastcgi-Cache $upstream_cache_status;
 
+  # Additional proxy header for WordPress (notably its Site Health check)
+  add_header X-Cache-Enabled $loopback_header_x_cache_enabled;
+
   # Specify a charset
   charset utf-8;