Sending signed and encrypted mails with Gnus to outlook users fails

Sending signed and encrypted mails with Gnus to outlook users fails

[Klaus Zeitler]

Hello,
when I send signed and encrypted emails with Gnus/SMime to
outlook users, outlook shows the following error:
 Your digital ID name cannot be found by the underlying security system

outlook users can read my signed emails or my encrypted ones but no
emails that are both signed and encrypted. Even more puzzling,
Thunderbird has no problems with these emails.

I'm wondering, if this is a problem with Gnus/SMime or with outlook.
Since Thunderbird is able to read the signed and encrypted emails
this looks like an outlook problem, but when I use Thunderbird
to send signed and encrypted emails they can be opened in outlook.
Apparently Gnus/SMime is doing something differently. I'm confused.

Has anybody seen something similar and is there a workaround or fix
for this problem?

Klaus

Re: Sending signed and encrypted mails with Gnus to outlook users fails

[Eric Abrahamsen]

Klaus Zeitler <klaus.zeitler@nokia.com> writes:

> Hello,
> when I send signed and encrypted emails with Gnus/SMime to
> outlook users, outlook shows the following error:
>  Your digital ID name cannot be found by the underlying security system
>
> outlook users can read my signed emails or my encrypted ones but no
> emails that are both signed and encrypted. Even more puzzling,
> Thunderbird has no problems with these emails.
>
> I'm wondering, if this is a problem with Gnus/SMime or with outlook.
> Since Thunderbird is able to read the signed and encrypted emails
> this looks like an outlook problem, but when I use Thunderbird
> to send signed and encrypted emails they can be opened in outlook.
> Apparently Gnus/SMime is doing something differently. I'm confused.

What you might want to do is do the sign-and-encrypt MIME thing, then
call `mml-preview' to see what the actual output is. Compare that to the
raw message produced by Thunderbird, and see if anything jumps out at
you.

Eric

Re: Sending signed and encrypted mails with Gnus to outlook users fails

[Eli Zaretskii]

> From: Klaus Zeitler <klaus.zeitler@nokia.com>
> Date: Mon, 23 May 2016 10:34:07 +0200
> 
> Hello,
> when I send signed and encrypted emails with Gnus/SMime to
> outlook users, outlook shows the following error:
>  Your digital ID name cannot be found by the underlying security system
> 
> outlook users can read my signed emails or my encrypted ones but no
> emails that are both signed and encrypted. Even more puzzling,
> Thunderbird has no problems with these emails.

Do both Emacs and Outlook run on the same system?

Re: Sending signed and encrypted mails with Gnus to outlook users fails

[Klaus Zeitler]

On Mon, May 23 2016, Eli Zaretskii wrote:

Do both Emacs and Outlook run on the same system?

No, nearly all my colleagues are Windows users and use either outlook
or Thunderbird, but I use emacs/Gnus on a GNU/Linux PC. The odd thing
is, that the Thunderbird users can read my encrypted+signed emails,
but outlook users can't.

Re: Sending signed and encrypted mails with Gnus to outlook users fails

[Eli Zaretskii]

> From: Klaus Zeitler <klaus.zeitler@nokia.com>
> Date: Tue, 24 May 2016 12:32:41 +0200
> 
> 
> On Mon, May 23 2016, Eli Zaretskii wrote:
> 
> Do both Emacs and Outlook run on the same system?
> 
> No, nearly all my colleagues are Windows users and use either outlook
> or Thunderbird, but I use emacs/Gnus on a GNU/Linux PC. The odd thing
> is, that the Thunderbird users can read my encrypted+signed emails,
> but outlook users can't.

Outlook running on Windows will use the system certificate store when
it wants a certificate, while programs running on GNU/Linux and ported
Posix programs might look in other places.  So you could have a
certificate that is known to one program and unknown to another.