Thanks for the explanation! I removed the entries for the certs in Actual and now it seems to be working. Solved a problem and learned something new!

OK, I noticed I had service1.duckdns.org --> Caddy IP configured in my local DNS for pihole, but didn't have an entry for service2. I added service2.duckdns.org --> Caddy IP. Not exactly sure how that works but now I can see errors in the logs for it in Caddy, and it's still sending me a 502.

I'm not really sure where to start troubleshooting based on the log entry:

{"level":"error","ts":1791273870.8226678,"logger":"http.log.access.log1","msg":"handled request","request":
{"remote_ip":"192.168.0.183","remote_port":"53434","client_ip":"192.168.0.183","proto":"HTTP/2.0","method":"GET","host":"service2.duckdns.org",
"uri":"/","headers":{"Accept-Encoding":["gzip, deflate, br, zstd"],"Sec-Fetch-Mode":["navigate"],"Sec-Fetch-Site":["none"],"Sec-Fetch-User":["?1"],"Te":["trailers"],
"User-Agent":["Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:155.0) Gecko/20100101 Firefox/155.0"],"Accept":["text/html,application/xhtml+xml,application/xml;q=0.9,*/*;q=0.8"],
"Upgrade-Insecure-Requests":["1"],"Sec-Fetch-Dest":["document"],"Dnt":["1"],"Priority":["u=0, i"],"Accept-Language":["en-US,en;q=0.9"],"Sec-Gpc":["1"]},
"tls":{"resumed":false,"version":772,"cipher_suite":4867,"proto":"h2","server_name":"service2.duckdns.org"}},"bytes_read":0,"user_id":"","duration":0.001651465,"size":0,"status":502,
"resp_headers":{"Server":["Caddy"],"Alt-Svc":["h3=\":443\"; ma=2592000"]}}

I don't think it's self-signed.. I used Caddy to generate the certs and copied them over into the config for the service. The service2 that I'm unable to access is ActualBudget and I followed their instructions from their docs (https://actualbudget.org/docs/config/https)

Probably an unpopular opinion, but The Departed. They dumbed down Infernal Affairs for western audiences. The shot of the rat at the end wasn't clever and the entire movie was like an unnecessary terrible Disney remake of an original that didn't need remaking.

Thanks for all the replies! The main features I was looking for were reminders to do things and having a centralized record of things that don't happen on a regular interval - like getting a roof fixed or putting in a new air-conditioner. Looks like DumbAsssets could be good for this, going to try it out!