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Encrypted Email: s/mime vs PGP

Get Secure Encrypted Email

There are two options for encrypting email. Which one you choose depends entirely upon what your needs are. Although I can make some suggestions for what works well on Macintosh systems.

S/Mime

This uses a secure certificate and works well for use on a Macintosh. I’ve found good success with using it. If you need to get your secure email on all your devices this is the option to choose. It will work on IOS devices like your iPhone and still do its job.

The cost varies but you have to shell out some dough for it. I found going with SSL.COM was a good choice. The cost was about $45 dollars for two years. Be sure to back up your private keys and keep them secure.

Both people who want to send email have to have the same setup with using S/Mime, the sender has to have the recipiants public key in their keychain to send mail.

To give someone your public key, send a signed message from your registered email address. Then the recipient can return your email with an encrypted message from the get go.

Always keep your private key secure.

PGP

PGP is a good choice for sending secure email if both people have the same setup. The one drawback is if you want to check your secure email on an IOS device, there is no way to decrypt messages on the iPhone with this set up and you will have to access your computer with your private key to read messages.

To give someone your public key, send a signed message from OpenPGP to the recipient and they will add your public key to their keychain. This will allow them to send you secure email that only you can read. And when you reply to them they will be able to read your email to them. This is granted that both people are using PGP.

The cost for OpenPGP is about $25 dollars and will work with the latest versions of MacOS Catalina. You can get it from: https://gpgtools.org

You can also send the PGP public key fingerprint and they can look up your address on the public key server.

Conclusion

Both options are pretty good, PGP takes some setup that is a little more involved and may be for advanced users. Be sure to install the Tools in the Apple Mail client so that you get the features of OpenPGP in your Mail client.

S/Mime is a good choice but requires valid certificates, and you have to renew them every year. If your certificate expires, you won’t be able to read previously sent messages, because they will be encrypted.

PGP works well on the Mac with Apple Mail, but requires a little more work on your part. It’s not difficult to do, you just have to read the screen a little more.

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