New pages sites default to "Only Accessible to Project Members" -> Automatic Lets Encrypt Certificates will not generate until the site is made public
I was attempting to set up a pages site and ran into this.
The current error messages are unclear "Error “Something went wrong while obtaining the Let’s Encrypt certificate”
I think we could write a more descriptive error that guards on this?
If pages site != public && auto_lets_encrypt_enabled == true
"Lets encrypt will not work unless your site is public. You can edit this in Settings."