Being fairly new to Lets Encrypt and the eco system around it Checkly is mostly being cautious. Having a none SSL encrypted dash for the trial is probably fine.
If this whole process runs super smoothly, we will lift this blockade.
Also, I come from the days where I had to call Verisign in Switzerland and fax in my passport details...
Just want to give the Lets Encrypt integration a bit of a trial period before going 100% in.
However, customers want to have https://status.example.com for their status pages. This is why we need to provide custom SSL certificates using Lets Encrypt.
In fact, we do this for our own SaaS and never had a problem. Our AWS instance is protected by *.mydomain.com SSL cert but we have other servers running on digital ocean etc. that have their own subdomains and their own SSL certs.
The tricky thing for us is to filter out the subdomains that we use (e.g. [blog,status,www]), and prevent our customers from using them as their own custom subdomains with our app otherwise our whole DNS redirection doesn't work.