SMIME.txt

F

f.puerner

Hi,

I used Apple Mail for years on my Office Mac (OS X 10.4.7). Since about
a year I digitally sign my mails with a certificate from AddTrust. No
problem with that configuration.

A few weeks ago I switched to Entourage 2004 (all patches installed)
with the account configured as an Exchange account. Our mail server is
Exchange 2000 (all SPs and patches installed). Now when I look at my
"sent items" in Windows Outlook 2003 at home, all my sent mails are
empty and have a file "SMIME.txt" attached.

What's going on?

Florian
 
D

Diane Ross

I used Apple Mail for years on my Office Mac (OS X 10.4.7). Since about
a year I digitally sign my mails with a certificate from AddTrust. No
problem with that configuration.

A few weeks ago I switched to Entourage 2004 (all patches installed)
with the account configured as an Exchange account. Our mail server is
Exchange 2000 (all SPs and patches installed). Now when I look at my
"sent items" in Windows Outlook 2003 at home, all my sent mails are
empty and have a file "SMIME.txt" attached.

What's going on?
Click to expand...

Check out the guide, "Getting Started with S/MIME on Entourage".

<http://www.entourage.mvps.org/smime/index.html>
 
C

Chris Ridd

Check out the guide, "Getting Started with S/MIME on Entourage".

<http://www.entourage.mvps.org/smime/index.html>
Click to expand...

That hardly begins to explain why Outlook/Exchange would start treating
signed messages as empty messages containing a file.

Entourage constructs signed messages in one of two ways, depending
whether the "send clear text" option's set in the Sender's mail account
properties. (Encrypting messages is a whole other can of worms.)

The first way (containing clear text) sets the whole message as
multipart/signed, then all the original parts of the message are
included as normal parts (eg text/plain) and finally there's an
application/pkcs7-signature part with a suggested filename of
"smime.p7s".

The second way (no clear text) sets the whole message as
application/pkcs7-mime with a suggested filename of "smime.p7m".

(The OP doesn't say which setting he/she's using.)

Presumably the "SMIME.txt" file is actually the
application/pkcs7-signature or application/pkcs7-mime part, though the
change of filename seems a bit gratuitous. If the OP saves one of those
files from Outlook and fixes the extension to p7s or p7m, is Outlook
then able to do something with them?

I'd guess that some sort of config's changed in Exchange such that it
doesn't correct recognize S/MIME types any more.

Cheers,

Chris
 
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