Cloudflare SaaS custom hostname 525

Hi. I'm trying to test out Cloudflare SaaS with custom hostnames for a new feature of mine. I'll write out what I've currenlty done.

  1. Created a fallback origin https://proxy-fallback.fivemanage.com/. This is an A record to a IP where the page is running on a caddy webserver.
  2. Created a CNAME customers to proxy-fallback.fivemanage.com .
  3. Created a custom hostname whitelist.error-interactive.com that is a CNAME record to customers.fivemanage.com.
FYI: In this case both domains go through CF and all the records mentioned here are proxied.

Now, if I go to the fallback domain, we see the webpage, if I go through whitelist.fivemanage.com, its just a 525 handshake error.

I've tried to enable Total TLS with Google Trust Services, without that working - disabled again.

Am I missing some certificates? I have not touched anything related DCV. Neither did I add any TXT records for error-interactive.com domain. Could it be related to Caddy? (I'm open to change to anything else if need be).

Would be great if someone could give some pointers. (Scream at me if I'm duplicating a post, couldn't find any) 🙂
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