[Discuss] SSL problems with imapfilter after upgrade to Debian 11

[richard.pieri at gmail.com (Rich Pieri)]

On Sat, 28 Aug 2021 01:54:15 -0400
Matthew Gillen <me at mattgillen.net> wrote:

> will tell you a fair bit about what the server is presenting to
> clients. (check the expiration on the cert; LetsEncrypt is only valid
> for 90 days; maybe your auto-renew is broken?)

SSL is working correctly. Auto-renew is working correctly. Not
switching to STARTTLS. My other IMAP clients work just fine, it's only
imapfilter.

https://github.com/lefcha/imapfilter

And... I finally figured it out. Debian's most recent incarnations of
imapfilter or OpenSSL are being too strict about hostname matches and
bombing out and not providing useful error messages.

But I also found a better workaround: tell imapfilter not to cache the
server certificate (options.certificates in the config file). Why this
works? Dunnow, but it does.

-- 
Rich Pieri