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GPG Mail: gpg: signing failed: Inappropriate ioctl for device

• Edit

Taylor Banks

04 Feb, 2019 05:39 PM

Using nightly build from yesterday, getting this error when attempting to sign and send any emails.

Even when I disable message signing (in the new message window, not in preferences), I get the same error.

Reinstalled nightly again, no change in behavior.

Expected
Messaged signed and sent.

macOS                   10.14.3     18D42
GPG Suite               2018.5      2397n   (6f26711)
GPG Mail                3.0.1       1349n   (c31a67f1)  28 trial days remaining
GPG Keychain            1.4.6       1522n   (59ac82d)
GPG Services            1.11.6      1062n   (7d585af)
MacGPG                  2.2.12      923n    (81ef14e)
GPG Suite Preferences   2.1.4       1082n   (c119ddd)
Libmacgpg               0.8.7       897n    (5e2fc45)
pinentry                1.1.0       33n     (6a7ab8b)

1. Support Staff 1 Posted by Steve on 04 Feb, 2019 07:11 PM

   

   Hi Taylor,

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

   It seems you installed a custom gpg version with fink/macports/brew/homebrew/from source? Could you remove it, repeat the steps and see if you are still running into the error message.

   Best,
   Steve

   • Edit

2. 2 Posted by Taylor Banks on 04 Feb, 2019 08:12 PM

   
   Steve, 

   
   

   I do use and rely on the cli version installed via homebrew. Why can GPGSuite not play nice with pre-installed gpg binaries?

   
   

   I'm not willing to sacrifice the version installed by brew, as homebrew's gpg seems to be updated much more regularly, and there are components that I use from the cli that do/did not seem to be installed or managed by GPGSuite. I also use and rely on keychain ( https://www.funtoo.org/Keychain ), which never seemed to work properly with GPGSuite's gpg-agent (based on past experience).

   
   

   Is there a way to have both? Please advise.

   
   

   Best,

   Taylor

   
   

   On Mon, Feb 4, 2019 at 12:11 PM Steve <[email blocked]> wrote:
   

   // Please reply above this line
   ==================================================
   From: Steve (Support staff)
   Subject: GPG Mail: gpg: signing failed: Inappropriate ioctl for device
   
   Hi ,
   
   welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.
   
   It seems you installed a custom gpg version with fink/macports/brew/homebrew/from source? Could you remove it, repeat the steps and see if you are still running into the error message.
   
   Best,
   Steve
   
   
   
   View this discussion at our support site online: https://gpgtools.tenderapp.com/discussions/nightly/1700-gpg-mail-gpg-signing-failed-inappropriate-ioctl-for-device
   
   
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   • Edit

3. Support Staff 3 Posted by Luke Le on 05 Feb, 2019 04:19 PM

   

   Hi Taylor,

   it is possible to have both but since GnuPG itself starts some of the services it needs on demand, it might use one service from one version and the other from another version.
   What you can try is to move your gpg in /usr/local/bin/gpg and symlink our gpg there instead, so basically:

    sudo mv /usr/local/bin/gpg /usr/local/bin/gpg-homebrew
    sudo ln -s /usr/local/MacGPG2/bin/gpg /usr/local/bin/gpg
   

   That way it should be possible to use both version of gpg at the same time.

   • Edit

4. Steve closed this discussion on 21 Sep, 2019 10:52 AM.