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> So I have a question -- where will Let's Encrypt certificates not work?

They're very well supported. Won't work in Windows XP and Android versions lower than 2.3.6. https://community.letsencrypt.org/t/which-browsers-and-opera...

> This would be great, apart from apparent insurance regular certificates bring, which I still don't know how to claim.

To my knowledge, that insurance has never been paid out, from any SSL vendor. It's a marketing gimmick.




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