[Users] New Windows Users: S/MIME

Luke Robison lukerobison at gmail.com
Wed Jan 30 16:16:45 CET 2019

Andrej, Paul,

Thanks for the quick responses, I'm sure I'm being dense, but I'm still
stuck.  See below:

On Wed, Jan 30, 2019 at 3:29 AM Andrej Kacian <ticho at claws-mail.org> wrote:

> On Tue, 29 Jan 2019 17:51:23 -0600
> Luke Robison <lukerobison at gmail.com> wrote:
> > Now back to claws, I'm unsure if I should give claws the GPG path to
> > either gpgsm.exe or gpg.exe, but neither one has much effect.
> > Nothing has changed that I can see for encrypted or signed messages.
> > No error messages about bad or missing certificates.  I've selected
> > S/MIME as my preferred encryption.
> You shouldn't need to do this, all GPG "engines" should be
> autodetected, with correct paths to relevant programs set up. GPG has a
> mechanism (gpgconf.exe) for just that. Look for entries like this in
> the debug log, during startup:
> sgpgme.c:767:GpgME Protocol: CMS
> Version: 2.0.30 (req 2.0.4)
> Executable: C:\Program Files (x86)\GNU\GnuPG\gpgsm.exe
It looks like it is finding my GnuPG that I installed:

prefs_gpg.c:671:Can't disable gpg agent (no GPG_AGENT_INFO)
sgpgme.c:716:setting gpgme CTYPE locale
sgpgme.c:723:setting gpgme CTYPE locale to: en_US
sgpgme.c:730:setting gpgme locale to UTF8: en_US.UTF-8
sgpgme.c:741:setting gpgme MESSAGES locale
sgpgme.c:748:setting gpgme MESSAGES locale to: en_US
sgpgme.c:754:setting gpgme locale to UTF8: en_US.UTF-8
sgpgme.c:767:GpgME Protocol: OpenPGP
Version: 2.2.12
 (req 1.4.0)
Executable: C:\Users\robison\AppData\Local\gnupg\bin\gpg.exe
sgpgme.c:767:GpgME Protocol: CMS
Version: 2.2.12
 (req 2.0.4)
Executable: C:\Users\robison\AppData\Local\gnupg\bin\gpgsm.exe
sgpgme.c:767:GpgME Protocol: GPGCONF
Version: 2.2.12
 (req 2.0.4)
Executable: C:\Users\robison\AppData\Local\gnupg\bin\gpgconf.exe
sgpgme.c:767:GpgME Protocol: Assuan
Version: 1.0.0 (req 1.0.0)
Executable: C:\Users\robison\AppData\Roaming\gnupg\S.gpg-agent
sgpgme.c:767:GpgME Protocol: Spawn
Version: 1.0.0 (req 1.0.0)
Executable: /nonexistent

prefs_gpg.c:521:Saving GPG config

> Leave the GPG path in Claws Mail preferences empty, it is there for
> people who are using custom GPG installations, and as far as I know,
> should only be used to specify the program for PGP handling (gpg or
> gpg.exe), not for S/MIME handling.
> > Trying to send mail does give errors.  Simply trying to send a signed
> > message gives a "Secret key not found" error, so I suspect what I'm
> > running from the command line and what claws is running are two
> > different programs.  Running with --debug and checking the
> > claws-win32.log file doesn't do much either, see log excerpt below
> >
> > Any suggestions?
> Yes, in Claws Mail account preferences, you need to select S/MIME as
> your privacy system. The log excerpt below shows that you have PGPMIME
> or PGPInline set, because it is trying to use the OpenPGP protocol.

 Under Configuration->Preferences for current account->Account->Privacy the
Default Privacy system is set to PGP MIME, and in fact I have even tried
removing the PGP Inline plugin, so my only options or PGP MIME or None.  I
can also check the setting in the Compose window, and it is set to PGP MIME.

Despite all that, I still see "sgpgme_setup_signers: OpenPGP protocol".
And the "secret key not found" error.  Does this mean I'm not using PGP

Should I be concerned about the "no GPG_AGENT_INFO" note in the log?

> Now, I haven't tried using S/MIME on Windows Claws Mail in a while
> (and the gpg4win installer I just downloaded from their site does not
> even want to unpack to start installing for some reason, go figure), but
> I remember it worked just fine if you have the certificate matching the
> e-mail address you are using, the secret key that goes with the
> certificate, and the issuer certificate.
> If gpgsm.exe can see these and Claws Mail can find gpg programs (see
> above), signing and encrypting messages should work.
> > Luke
> >
> > procmime.c:2593:procmime_write_mimeinfo
> > sgpgme.c:590:sgpgme_setup_signers: OpenPGP protocol
> > sgpgme.c:600:using key for myemail at company.com
> > warning: setup_signers start: End of filealertpanel.c:253:Creating
> > alert panel dialog...
> > alertpanel.c:211:called inc_lock (lock count 2)
> > alertpanel.c:221:called inc_unlock (lock count 1)
> > compose.c:5407:called inc_unlock (lock count 0)
> >
> Regards,
> --
> Andrej
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