Nightly + Outlook 15.36.1 not working?

jdsmith1012's Avatar


28 Jul, 2017 09:52 PM

Version info is below.

I have an up-to-date stable Mac (non-beta) and started with the stable GPG Suite. I successfully imported my GPG key and secret from my Windows desktop and was able to successfully send a signed email from Apple mail. So I know it's working.

I then enabled GPG Services as I'm aware full integration with Outlook is not available at this time.

I only need to sign emails. Preferably with the signature inline in the email (not as an attachment or part of a header, if possible).

I opened a new draft, typed some text, and selected all the text. Once done, I right clicked and went to services and found the "Sign Selection" option. I select this and I am prompted for my password but nothing is added to the email. In fact, outlook seems to freeze.

I upgraded to the beta with the same result. I then upgraded to nightly which still has same result.

Two questions:

1) How can I get email signing to work (to any capacity) with Outlook and GPGServices?

2) Is there a way to just go to services and "Sign email" instead of having to select all the text first? Some screenshots I see online show a "Sign" option in addition to the "Sign Selected" option I just don't see it.

Version Info

macOS 10.12.6
GPG Suite 2017.1 (1939n)
GPGServices 1.11 (954n)

  1. Support Staff 1 Posted by Steve on 31 Jul, 2017 12:21 PM

    Steve's Avatar

    Hi jdsmith1012,

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

    We have a ticket for this problem. I connected this discussion with the existing ticket. That means, should this discussion get closed, it will be re-opened as soon as the ticket is closed. That way you'll stay in the loop and get notified as soon as we have news. Feel free to open a new discussions should you run into further problems or need assistance.

    As a workaround you can formulate your mail in Outlook, copy the text to, sign / encrypt there and then copy the signed / encrypted messages back to Outlook.

    All the best,

  2. Steve closed this discussion on 22 Oct, 2017 02:18 PM.

  3. Support Staff 2 Posted by Steve on 08 Jan, 2018 07:14 PM

    Steve's Avatar

    Hi jdsmith1012,

    we took a closer look at this problem. It seems Microsoft uses read-only windows in it's office suite for whatever reason. Thus GPGServices cannot write to neither the Word nor Outlook draft windows.

    It would be great if you could file this problem with Microsoft to make them aware that their office suite is no longer working as expected with GPGServices. In Outlook please select Help > Contact Support from the menu bar to file a request.

    There's a workaround for the time being if you depend on Microsoft Office: Instead of selecting Encrypt or Sign message, select Encrypt message to new window. That will result in the expected cypher or signed text, which then can be copied into work / outlook.

    All the best,

  4. Support Staff 3 Posted by Steve on 19 Jan, 2018 08:29 AM

    Steve's Avatar

    We have good news: The Microsoft Office update 16.9 fixes this known issue in their software. With that version it's again possible to use GPGServices as expected, the workaround to sign / encrypt to new window is no longer necessary.

    Sweet \°/
    Awesomeness restored.

    I'm closing this discussion. Should you need further assistance or have questions you can re-open this discussion here or open a new one any time.

    Have a great day,

  5. Steve closed this discussion on 19 Jan, 2018 08:29 AM.

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