tag:gpgtools.tenderapp.com,2011-11-04:/discussions/problems/13733-broken-attachments-in-microsoft-365-webmail-if-gpg-signed-smimeGPGTools: Discussion 2014-01-07T15:20:14Ztag:gpgtools.tenderapp.com,2011-11-04:Comment/302202882013-11-26T21:17:11Z2013-11-26T21:19:43ZBroken Attachments in Microsoft 365 webmail if GPG signed S/MIME<div><p>Hi Mac,</p>
<p>this is clearly a bug of office 365 and it would be best to
bring it up with Microsoft.<br>
You could enable inline PGP, in wich case the text is wrapped in a
signature and no attachment is created,<br>
but that's not encouraged, since the signature often breaks due to
manipulations by SMTP servers and attachments<br>
are NOT encrypted, only the message body if you choose to
encrypt.</p>
<p>The following article describes how to enable inline PGP if you
still want to try that:<br>
<a href=
"http://support.gpgtools.org/kb/faq-gpgmail/gpgmail-2-hidden-settings#enable-pgp-inline-for-support-of-legacy-mail-clients-important-for-windows-compatability-">
http://support.gpgtools.org/kb/faq-gpgmail/gpgmail-2-hidden-setting...</a></p></div>Luke Letag:gpgtools.tenderapp.com,2011-11-04:Comment/302202882013-11-26T21:51:31Z2013-11-26T21:51:31ZBroken Attachments in Microsoft 365 webmail if GPG signed S/MIME<div><p>Hi Luke, Yeah, I figured as much. But I also was thinking that
maybe the GPG team would be more responsive & produce better
quality product. :-)</p>
<p>At this time, I am just signing emails, not encrypting. So any
solution is welcome that allows the email to be signed without
breaking the attachments - no matter how lame the recipients
webmail is.</p></div>macmedixtag:gpgtools.tenderapp.com,2011-11-04:Comment/302202882013-11-27T01:46:29Z2013-11-27T01:46:29ZBroken Attachments in Microsoft 365 webmail if GPG signed S/MIME<div><p>I followed the link Luke provided & tried enabling inline
PGP, but that seems to knock out any other attachments. The
recipient does not even know I included an attached file. So
Thanks, but not a good solution for emails that include an attached
file such as a picture or document. It appears the only current
solution is to turn PGP signing off when the recipient is using MS
Outlook Web Mail, but of course I have no way of knowing. Since I
am just digitally signing emails not encrypting, and since a client
just switched to using MS 365 cloud email, switching off pgp may be
my only available option when I am sending files.</p>
<p>FWIW, I did file a bug report with MS, but I doubt they care
about Mac OSX nor Linux, nor ensuring their web app is compatible
with digitally signed emails. (sigh).</p></div>macmedixtag:gpgtools.tenderapp.com,2011-11-04:Comment/302202882013-11-27T18:16:26Z2013-11-27T18:16:26ZBroken Attachments in Microsoft 365 webmail if GPG signed S/MIME<div><p>I got a reply from MS Support. They don't care. It's not a tech
support issue.</p>
<p>This is Chris Munroe with Exchange Online support in regard to
service request 1224977378, regarding an issue with viewing s-mime
attachments. I apologize about any inconvenience, and have reviewed
your update. As we both agree this is by design with the current
version of Exchange Online and cannot be resolved by technical
support. If you would like to suggest this feature added to
Exchange Online please utilize the feedback link from within
Outlook Web App by clicking on the question mark toward the top
right of the screen. This service request will be closed as the
feature is unsupported currently.<br>
Thank you for contacting Microsoft Online Service support,</p></div>macmedixtag:gpgtools.tenderapp.com,2011-11-04:Comment/302202882013-11-29T11:36:30Z2013-11-29T11:36:30ZBroken Attachments in Microsoft 365 webmail if GPG signed S/MIME<div><p>Wow, nice support from MS. Macmedix: As Luke pointed out,
OpenPGP/Inline currently does not support attachments.</p>
<p>Since it is a un-documented standard it isn't really encouraged
to be used. I'm not even sure if there's anything on our side we
could do to improve the situation except for improving
OpenPGP/Inline.</p></div>Steve