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GPGMail and S/MIME?

• Edit

Bob Tanner

25 May, 2012 06:13 PM

Environment:

• Software name and version: GPGMail 2.0a30
• OS X version: 10.7.4

Is it possible to have GPGMail and S/MIME installed together and select which crypto technology to use when sending the email?

1. Support Staff 1 Posted by Steve on 27 May, 2012 02:38 PM

   

   Hey Bob,

   you might wanna consider installing the latest nightly. I think GPGMail 2.0a31 was the latest we included there. http://nightly.gpgtools.org/

   As for your question: S/MIME and OpenPGP can coexist peacefully in GPGMail 2.0.

   http://cl.ly/01093k3m2R1F0k0w3l22

   You should have a dropdown on the top right which let's you select, which method you want to use.

   Does this help?

   All the best,
   steve

   • Edit

2. 2 Posted by Bob Tanner on 01 Jun, 2012 04:46 PM

   

   Hi Steve,

   Thanks for the reply. I tried looking at the link,

   http://cl.ly/01093k3m2R1F0k0w3l22

   But all I get is

   CloudApp
   Sorry, no drops live here.

   Perhaps the link you clicked was broken or the owner of this drop has deleted it.

   What was there a screenshot?

   I'll take look at the nightly. Thanks again.

   • Edit

3. Support Staff 3 Posted by Luke Le on 01 Jun, 2012 04:53 PM

   

   Hi Bob,

   you can try if these screenshots work:

   1.) S/MIME | PGP select

   http://cl.ly/1c0639062F3O1z2p2m06

   2.) S/MIME selected

   http://cl.ly/1b0R1v1l1A262W182b1H

   3.) OpenPGP selected

   http://cl.ly/0w1I0g0y2B1e0v3C0d0h

   • Edit

4. 4 Posted by Bob Tanner on 01 Jun, 2012 05:32 PM

   

   This one works for me:

   http://cl.ly/1c0639062F3O1z2p2m06

   Installed GPGMail 2.0a31 Build 107103

   I do get the OpenPGP and S/MIME options (screenshot below)

   https://skitch.com/basictheprogram/86dt4/fullscreen

   But notice the sign (check mark) and encrypted (lock) are greyed out (orange box). Is there anything else I need to do to activate S/MIME when I have GPGMail installed?

   I'll add to this that when I go into the Keychain Access app it put my S/MIME certificate into the CA Keychain and under Category is shows up under Certificates and All Items.

   Nothing showing up in Console either other then the standard GPGMail info.

   • Edit

5. 5 Posted by Bob Tanner on 01 Jun, 2012 06:50 PM

   

   Had a co-worked setup S/MIME and he does not have GPGMail installed and signing and encrypting via S/MIME works for him.

   Just circumstantial evidence that GPGMail is the cause of S/MIME not working for me.

   • Edit

6. Support Staff 6 Posted by Luke Le on 01 Jun, 2012 07:24 PM

   

   Hmm... if you remove GPGMail, does S/MIME work for you?
   Could you please test that?
   It's important that your "From" address exactly matches your S/MIME certificate.

   • Edit

7. 7 Posted by Bob Tanner on 01 Jun, 2012 08:35 PM

   

   I read about the case folding and what not. I've verified that my email address and cert are exactly the same.

   Removing GPGMail and now I don't get the encrypt or sign icons on the compose window. How odd!

   So it looks like something outside of GPGMail but still something busted in Mail.app for me.

   /edit

   My co-workers is using Snow Leopard I'm on Lion

   • Edit

8. Support Staff 8 Posted by Luke Le on 01 Jun, 2012 08:50 PM

   

   That's what I expected. For some strange reason Mail.app's S/MIME implementation is very fragile. Sometimes it suddenly stopped working for my S/MIME keys. Re-importing helps, so you could try that.

   But in this case I think it's unrelated to GPGMail. Once Mail.app recognizes your S/MIME keys and presents you the lock and sign buttons you should be set to try it with GPGMail again.

   • Edit

9. 9 Posted by Bob Tanner on 04 Jun, 2012 05:19 PM

   

   Finally got everything to work. I had to use certificates from https://www.startssl.com/. For the next person that needs to work on this here is a list of links I used to resolve my problem.

   Get a free certificate here.

   https://secure.comodo.com/products/!SecureEmailCertificate_Signup

   Follow directions here.

   http://arstechnica.com/apple/2011/10/secure-your-e-mail-under-mac-o...

   Trouble importing certificate? Look here.

   http://www.hoylen.com/articles/it/email/security/mail.html

   Very helpful links, especially about using firefox
   http://krypted.com/mac-os-x/smime-in-os-x-isnt-just-for-tin-hat-wea...

   http://krypted.com/mac-os-x/smime-in-os-x-lion/

   • Edit

10. Support Staff 10 Posted by Steve on 04 Jun, 2012 05:24 PM

    

    Wow. This looks like a long read. Glad you were able to solve this and thanks for posting all the links. They'll be very useful to other users.

    Closing. :)

    • Edit

11. Steve closed this discussion on 04 Jun, 2012 05:24 PM.