Encryptomatic OpenPGP is an Outlook add-on that provides robust email encryption. It connects with open PGP key servers and is free for personal use, with a low price for everyone else. Give it a try!

One of the best things about this add-in is that it integrates seamlessly with the Outlook toolbar, so you won't need to go searching for it whenever you want to use it. Whether you're generating a new key pair or importing an existing one, you can easily do so with just a few clicks.
One of the features that really sets this software apart from others is its ability to configure sending rules. This means you can easily specify which emails should be encrypted and which should be sent in clear text, helping to ensure your messages are always secure.
If you're looking to upload or retrieve keys from open key servers, this add-in has got you covered. It's also compatible with both Enigmail and PGP, so you can be sure it'll work with whatever other email security tools you may be using.
If you do encounter any issues while using this add-in, don't worry—there's email and telephone support available from the team at Encryptomatic LLC. And best of all, it's free for personal, journalist, and activist users, making it an excellent choice for anyone who wants to keep their emails secure. For everyone else, it's still an affordable option that's well worth trying out.
Version 1.5.7:
Add additional key servers.
Open sent encrypted emails from Outlook inbox
various optimisations and fixes.