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There was an issue with LetsEncrypt a while back (end September?) replacing one of its root certificates. They did everything right to the documents, but...

 

Older versions of SSL libraries had a bug where if they tested one cert in the chain and it had expired (or was otherwise wrong), it failed the certification, even if there was another certificate in the same chain that was valid for that path. Apple's older OSes have that buggy SSL library.

 

Apple has decided to fix only those systems that are not "expired", knowing that old iThings will now break with "insecure certificate" on a massive number of websites (because LetsEncrypt is easy to use, common and (importantly) *free*). BBO is one of them.

 

It's not something BBO can do anything about, unfortunately. searching for "mac letsencrypt" will likely give you some fixes you can do yourself, *if you are suitably technical*. None of the solutions I have seen are "easy for nontechies", plus they all are "make a mistake and you can cause even more problems". Just live with it if you read it and don't *thoroughly* understand what they're asking you to do and why.

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