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Re:Let's Encrypt has turned on stricter validation requirements by Crosseye_Jack on Wednesday February 19, 2020 @10:48PM (#22372530)
If you give an email address to your LE client you should get an few emails from LE advising you when a cert is due to expire giving you some time to get it sorted before your old cert expires.

Edit: personally I also have a script that runs every day and checks the validity of all the certs in my live directory and pings me when they are due to expire as a second measure.

Re:Let's Encrypt has turned on stricter validation requirements by LukeShu on Thursday February 20, 2020 @12:07AM (#22372830)
I most of the LE/ACME breakages I've seen, the issue was that something broke in certbot (or other client) when rotating in the new cert, not that it was unable to get a new cert issued. LE won't email you about that.
Re:Let's Encrypt has turned on stricter validation requirements by Crosseye_Jack on Thursday February 20, 2020 @12:22AM (#22372895)
Which is why I monitor the live certs expiry dates as well. But that’s a bug with the client then with LetEncypt.