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Re: Microsoft Outlook Vulnerability: S/MIME Loss of Integrity
From: Patrick Dunstan <patrick.dunstan () gmail com>
Date: Mon, 17 Jun 2013 23:02:40 +0930

Completely agree with your sentiments here, Valdis.

The error messages given to everyday users are completely ridiculous in
most cases. I feel though with the padlocks and green bars in browsers
nowadays, there has at least been some effort made to make security
understandable for the average user out there. But you're right in saying
so much more is needed/could be done.

What bewilders me in 2013 is that email has been completely left behind. As
if to say "everyone accepts it as insecure so we just wont worry about it".
But if you don't work in IT, lets be honest, most people out there do
actually believe email is secure and don't think twice about it. If
encryption and trust are so part and parcel on the web, why has email been
so left in the dark?

Case in point: Google don't even offer support for S/MIME in GMail and it's
probably the most widely used online email service available today.

On Mon, Jun 17, 2013 at 10:23 PM, <Valdis.Kletnieks () vt edu> wrote:

On Sun, 16 Jun 2013 00:51:10 +0930, Defence in Depth said:

Microsoft Outlook (all versions) suffers from an S/MIME loss of integrity
Outlook does not warn against a digitally signed MIME message whose X509
EmailAddress attribute does not match the mail's "From" address.

Congrats on the technical side, for spotting this.

On the flip side, there are a number of cases where the signer address
legitimately does not match the From: address. For instance - if the
signer is
listed in Sender: instead of From:, if it has passed through a mailing list
that rewrites the From: line, or some combinations of resends and
forwards. And
yes, a lot of this sort of crap is only semi-legit because it's coming from
misconfigured servers - but operational reality dictates that you have to
deal with the fact that there's a *lot* of  (And we'll overlook the
fun and games available due to the distinction between an RFC821 MAIL FROM:
and and RFC822 From: line).

I suppose it could be worse - it's been a few years since I last saw a
address in an e-mail.

A few operational notes regarding alerts in user-facing software:

1) A lot of browsers used to display broken padlocks when SSL failed. They
don't do this anymore because users *will not* look at that sort of subtle

2)  They'll look at a big pop-up that obstructs their view - but only if it
happens so rarely that they have to call somebody and ask "wtf is this?".
If it
becomes a "oh it does this once every week or two" click-through, it's now
become "worse than useless".

As you noted, most browsers will notify the user if the browser detects a

What you gloss over is that browsers *totally suck* at presenting that
in a way that is both understandable and actionable to a general user. Just
yesterday I had Firefox alert on a SLL certificate mismatch, and it gave
me the
helpful info that the certificate presented was only valid for *.
Now, *I* know exactly what happened there, and *you* know, and the guy who
pushed some content to Akamai without looking to see if there were https:
pointing at the content will go "D'Oh!" when he finds out - but if you're
Sixpack and don't know if Akamai is a box in your ISP's server room or a
box in
a server roomin the Ukraine, you got nothing.  And if you get enough of
totally annoying pop ups, you'll just learn to click through without

Bottom line:  yes, it would be nice if all this sort of stuff was more
deployed and enforced.  But given that we've tried this with dismal results
with Windows UAC alerts, firewall alerts, browser alerts, and A/V alerts,
there's no real reason to expect that *this* time we'll actually get it
for MUA alerts.

Bonus points for the most creative suggestion for how to leverage a *fake*
From:/signature mismatch alert into a compromise (a la fake AV alerts that
you to download actual malware).

Really - Outlook may do this wrong, but I don't think we as an industry
a frikking clue how to actually do this right.

Patrick Dunstan
Full-Disclosure - We believe in it.
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