Following up on this for anyone who may stumble on it in the future. The issue was not anything to do with the Layer4 configuration, but that I was redirecting traffic to three different servers all using their own certificates for the same wildcard domain, which caused browser issues when going back and forth across servers.
Everything works now that I've specified each individual subdomain in my Caddyfile vs using *.halp.app.
Everything works now that I've specified each individual subdomain in my Caddyfile vs using *.halp.app.