All my letsencrypt certificates in IIS stopped working today

The problem is definitely within your system.

As unusual as it may seem, to me there can only be a few places where things could go this way:

  • IIS
    [has anything changed recently]

  • certificate store
    [has anyone added/removed any certs recently]

I'd review recently applied Windows Updates for anything cert related.
I'd also try issuing a cert from another CA to see if the LE is actually part of this problem [or not].

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