N8N102 Webhook Checker doesn't like Tailscale Tunnels

Working through N8N102 and on the section 2 hands on exercise. I have my n8n exposed via a tailscale tunnel and the webhook checker will not play nice. I’ve used claude to confirm that other systems are able to reach my n8n but the checker doesn’t, it piloted using the checker and confirmed its just that server that won’t talk to a tailscale funnel. I installed a temporary cloudflare funnel and everything cleared fine, meaning its not the workflow or config thats the problem. Any insight?