Mac Outlook 2011 Support

dajenik's Avatar


02 Apr, 2015 11:47 PM

Has anyone figured out how to use GPG to support Outlook 2011? Is there anyway to import the GPG key chain elements (certificates and keys) into the Mac Keychain access app? This should allow me to add the certs to the Outlook client for digital signatures and encryption. I've seen the export GPG Keychain export function but I'm unable to import them into a keychain within the Mac Keychain Access app. What am I missing on this?

  1. 1 Posted by dajenik on 26 Apr, 2015 10:27 PM

    dajenik's Avatar

    In a post by Tino from back in September 2014, using the general services to sign, encrypt and decrypt was presented (link below)

    However, in Outlook 2011 under tools/accounts/advanced/security, Outlook provides the user with an integrated approach which only requires the user to select the necessary certificates for these actions. Unfortunately, the only certificates shown are those int he Apple Keychain Access and although it does allow the user to select other certificates, for some reason, it does not recognize the GPG exported keys. Is that because the GPG is user signed and does not include a third party CA? Anny thoughts on how to make this work would be greatly appreciated. Thanks.

  2. Support Staff 2 Posted by Steve on 02 May, 2015 05:51 PM

    Steve's Avatar

    Hi Dajenik,

    I think here's a misconception in usage of S/MIME certs and OpenPGP keys, which are not the same thing.

    I think what you describe is Outlook supporting S/MIME certs. If you have to use Microsoft Outlook on your mac, I think Symantec's Encryption Desktop software supports that.

    GPG Suite comes with GPGMail which integrates into Another alternative is Thunderbird with the Enigmail plugin.

    Or you could use GPGServices as a workaround:

    All the best,

  3. 3 Posted by dajenik on 04 May, 2015 02:32 PM

    dajenik's Avatar

    Understand there is a difference. I assumed that Outlook 2011 supported both S/MIME and PGP if the certs were made available in the Apple Keychain Access. Apparently a bad assumption on my part; I should've known better given Microsoft's past track record. I've used Enigmail and I like Thunderbird but as with many I was nudged onto the MS Outlook path and was simply looking for a solution. I've used the service approach and it does work just not integrated. Thanks for you prompt reply.

  4. Support Staff 4 Posted by Steve on 02 Jun, 2015 12:37 PM

    Steve's Avatar

    Well you are free to choose your mail client. works most fluent and GPGMail integrates nicely. Thunderbird is fine as well.

    Maybe you want to give a try. You can always switch back.

    Closing this discussion. If you have more questions you can always re-open or create a new discussion.

  5. Steve closed this discussion on 02 Jun, 2015 12:37 PM.

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