For the past 3-4 years I've been using (and still use) Thunderbird + gnupg + enigmail. This has made it completely painless and transparent to use signed/encrypted email with nigh-zero overhead (check the option saying "encrypt message" if you want to encrypt it, or set it to encrypt always). This makes taking communications security seriously super easy.
One downside to this for business use is that Lightning, the Thunderbird calendar application, sucks. It sucks big time. Super big time. It's just awful.
The best I've seen for (Windows) based calendar management tied into email is Outlook. But the flipside of this is I have yet to see a good/painless implementation of gpg/pgp for Outlook.
Can anyone offer any advice?
Open Source/GPG based is preferred. but if a pay plugin for PGP is what is needed, I will begrudgingly accept that as well.



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