PKI (CAC) signed Entourage messages being filtered by various e-mailservers...

M

Mark Radleigh

Greetings all,

I'm having an issue with various sites running Exchange 'filtering' out any
message I send that is PKI (CAC specifically) signed. Specifically, I am
told that 'they' delete any message that is unscannable but it should NOT
effect signed/encrypted messages. I have done various tests with different
encoding settings for attachments and mail formatting settings (i.e. plain
text or html) with no luck. E-mail from Outlook (running on a Windows
machine) or the 'Mail' program that is found on the Mac seem to work. I am
attempting work with 'them' to at least get logs to find out what is going
on (no luck yet), but I shouldn't have to if they aren't having problems
with other mail clients (previous encounters with this issue point to the
message being 'unscannable' for some reason).

So my question is: "What is Entourage doing 'different' to the messages that
is causing it to be 'filtered'"?

I have analyzed the message source from Entourage sent messages (via
'Message->Source' on the message in the 'Sent Items' folder) and 'Outlook'
or 'Mac Mail' messages and can only thing I can see (besides the obvious
header differences) are the order of some headers and the following message
that is in the Entourage message:
This message is in MIME format. Since your mail reader does not understand
this format, some or all of this message may not be legible.


The full body of a problem PKI signed message (with irrelevant and/or
sensitive text deleted) is:

------- <BEGIN MESSAGE SNIPPET> -------
User-Agent: Microsoft-Entourage/12.12.0.080729
Date: Tue, 09 Sep 2008 09:56:39 -0400
Subject: TEST - CAC signed message #2...
From: Mark Radleigh <xxxx>
To: XXXX
CC: Mark Radleigh <xxxxx>
Message-ID: <C4EBF8D7.22362%xxxxx>
Thread-Topic: TEST - CAC signed message #2...
Thread-Index: AckSg+F/4035rq9FRkqOGezRO+qrDA==
Mime-version: 1.0
Content-type: multipart/signed;
protocol="application/pkcs7-signature";
micalg=sha1;
boundary="B_3303799000_5195855"
This message is in MIME format. Since your mail reader does not understand
this format, some or all of this message may not be legible.

--B_3303799000_5195855
Content-type: text/plain;
charset="US-ASCII"
Content-transfer-encoding: 7bit

[text deleted]

--B_3303799000_5195855
Content-type: application/pkcs7-signature; name="smime.p7s"
Content-transfer-encoding: base64
Content-disposition: attachment;
filename = "smime.p7s"

[text deleted]

--B_3303799000_5195855--

------- <END MESSAGE SNIPPET> -------

Anybody have any ideas or suggestions? I'm lucky that the 'other end' is
willing to at least make an effort to see what's going on (no guarantee of
changing anything though), but their default stance (pending a simple fix)
is '...we don't support Mac, only Windows xxx systems...' (plus who knows
what other e-mail servers are doing the same thing).

Perhaps I should take this as a 'hint' that the internet just filtering me
out of existence. :eek:


Thanks,

Mark Radleigh
 

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