Using GPG keys with Gmail and what's the difference between S/MIME certificates and OpenPGP keys?

nittin's Avatar


24 Feb, 2019 06:44 PM

I would like to use my gpg key with gmail. how would i go about doing that? can't seem to find gpgsm on my system (osx 10.12.6) I've seen that gpg and smime do not like each other. something about an apple not being able to talk to an orange. Is there any hope that i will be able to use the key from gpg in gmail?

  1. Support Staff 1 Posted by Steve on 25 Feb, 2019 10:49 PM

    Steve's Avatar

    Hi nittin,

    welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.

    OpenPGP and S/MIME can co-exist and be used aside each other in And OpenPGP is agnostic to the email provider you may be using. You can create keys for any email you want and for as many email address you need.

    Here's our Getting Started Tutorial which is a good starting point if you are a new user.

    If you run into trouble, don't hesitate to ask away.

    All the best,

  2. Support Staff 2 Posted by Steve on 25 Feb, 2019 10:50 PM

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    What do you mean with "can't seem to find gpgsm"? If you had S/MIME setup but can't find any trace of it, you can try re-importing your S/MIME cert to macOS keychain.

  3. 3 Posted by Nittin Rogbeer on 26 Feb, 2019 03:13 AM

    Nittin Rogbeer's Avatar

    Hi Steve,

    There’s an option to upload smime keys into gmail but they need to be in
    the p12 format. Is there a way for me to export my keys from gpg keychain
    into the p12 format instead of asc?


  4. Support Staff 4 Posted by Steve on 26 Feb, 2019 11:50 AM

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    No. OpenPGP keys are not to be confused with S/MIME certificates, which are indeed in the p12 format. But those keys / certificates are not exchangeable and are two different technologies.

    This security stackexchange thread covers the questions how OpenPGP and S/MIME differ:

    You should be able though to use S/MIME directly in No need to use the gmail webmail for that.

  5. 5 Posted by Nittin Rogbeer on 26 Feb, 2019 12:41 PM

    Nittin Rogbeer's Avatar

    Hi Steve,
    Thanks a lot for your help. Is it a planned feature that openPGP would
    generate S/MIME certificates? I’ve read somewhere that one can use pgpsm to
    create those. Unfortunately it doesn’t seem to be installed on my computer.
    I even saw that in the pgp manual. Please help me.

  6. Support Staff 6 Posted by Steve on 26 Feb, 2019 02:16 PM

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    OpenPGP and S/MIME are two different technologies. So no, OpenPGP will never generate an S/MIME certificate.

    I am not familiar with a software called pgpsm, so can't say anything about that.

    Which manual are you referring to? Can you share a link?

    I am not quite sure which problem you are trying to solve. So have you created an OpenPGP key already? And if yes, is there anything not working for you?

  7. 7 Posted by Nittin Rogbeer on 26 Feb, 2019 03:09 PM

    Nittin Rogbeer's Avatar
  8. 8 Posted by Nittin Rogbeer on 26 Feb, 2019 03:10 PM

    Nittin Rogbeer's Avatar

    there seems to be an option in there to export p12 files? am i missing

  9. Support Staff 9 Posted by Steve on 26 Feb, 2019 03:31 PM

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    That is a command line utility. If you want to use S/MIME with your gmail webmail you need to get an S/MIME certificate. That would be completely unrelated to OpenPGP.

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