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Everyone is offering this happy path. And people do pay for it, but the market price for "a Lets Encrypt cert on my site" is $0. It's mostly just a great way to get people started on a more valuable service.

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Lets Encrypt works fine for personal sites, etc. but it absolutely crushes the use case of being a large scale service needing to support thousands of individual sites, each with their own SSL cert.

Heroku, Hubspot, Shopify, etc. all have implemented LetsEncrypt and UX wise, is now pretty much just the default.

Yup. I use LetsEncrypt for 12 sites with their own individual certs, and even that gets painful, but managable.

If that is painful, you should have automated it. I don't even know how many certs I have ATM (maybe 20 or 30 or so), because it's so easy to add new domains. I described my setup here: https://blog.bethselamin.de/posts/how-i-run-certbot.html

Don't forget the 90 day bot generated event to update your cert

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