I see it as a matter of severity. Malware attacks are, as you say, extremely 
common. They are also fairly easy to guard against (assuming the users do what 
they are told <ahem>) and even at that the majority are more annoying than 
threatening. The cost to guard against them ranges from very cheap (free SpyBot 
or Ad-Aware) to blocking at the firewall or using a content proxy. 
>From what was said in the first post the inconvenience in this solution of 
>guarding against a MitM attack is that some users have to give up using their 
>browser of choice. If that’s the only problem with the solution I say move 
>forward; a handful of stalwart Safari users should not be able to hold the 
>company’s security hostage. And if it’s a titled person doing it he’s doing 
>the company a disservice.
But in deference to your management that likes things categorized, labeled, 
enumerated and fully known to the nth degree so a dollar cost per percentage of 
likelihood can be attached... there is no answer. Not all MitM attacks are 
reported but rather handled quietly. How many security issues have you run into 
over the years (up to and maybe including MitM)? How many did you write up and 
report in such a way that some future person could look up statistics based on 
the aggregate of such occurrences including yours? Zero, right? Unless the 
reporting was actually part of your job description or there was something 
unique or interesting about the attack you just handled it and moved on like 
the rest of us do as we juggle umpty-hundred issues in a given time frame. The 
statistics are not available no matter how much your management may want it 
otherwise; the decision has to be made based on the consequences of the attack 
rather than the likelihood of it. Said consequences are potentially highly 
severe and injurious to the company.
As someone else pointed out – the consequence of a MitM can and does include 
compromising network security to the point where the CFO’s workstation could be 
burglarized; account numbers and passwords - wouldn’t that be lovely? The 
overhead of accomplishing a successful MitM attack means the attacker’s intent 
is something a good deal more serious than a piece of malware that steals the 
user’s home page; don’t let management suck you into that apples to grapes 
comparison.
Again, if the only objection to the solution is a handful of obstinate users 
those users can go pound sand.
I have never experienced a kitchen fire but always have a fire extinguisher 
available. I don’t care what the odds are of it happening; I do not wish to 
deal with the consequences of not being prepared for one. Keeping a fire 
extinguisher available is a small price to pay for preparedness. S*** happens; 
the wise man always keeps a roll of TP handy rather than weigh the odds of it 
happening at the wrong time and not carry a roll.

From: David Lum 
Sent: Thursday, August 01, 2013 9:28 AM
To: [email protected] 
Subject: RE: [NTSysADM] man-in-the-middle attack

What I mean is the inconvenience of increased security work the risk? An 
extreme example is “computers can get infected via the Internet…let’s 
disconnect from the Internet”. The risk of one of 500 systems getting malware 
from the Internet over any six month span is almost 100%, but the loss of 
business exceeds the most likely losses from being hit by malware.

 

If a specific attack happens only once per 100,000,000 businesses in a six 
month span (I have no clue on MITM, Googling “business exploited by 
man-in-the-middle” only returns how serious it is but I am unable to find 
actual examples), is it worth worrying about?

 

It’s like hearing Diet Coke “it’s so bad for you it can kill you instantly”, 
but not having any actual examples to back it up.

 

I’m not saying I don’t want to do this, but if management asks how likely it is 
to get exploited I’d like to give them *something*.

 

 

From: [email protected] [mailto:[email protected]] On 
Behalf Of Ken Schaefer
Sent: Wednesday, July 31, 2013 4:06 PM
To: [email protected]
Subject: RE: [NTSysADM] man-in-the-middle attack

 

> In any event, the odds are irrelevant - the issue is the business risk of 
> intrusion/loss. 

 

How can you say that “odds are irrelevant” if the issue is business risk? 

 

Risk is “potential for loss”, and potential includes a weighting for likelihood 
(i.e. “the odds”)?

 

Can you clarify what you mean?

 

Cheers

Ken 

 

From: [email protected] [mailto:[email protected]] On 
Behalf Of Micheal Espinola Jr
Sent: Thursday, 1 August 2013 1:43 AM
To: [email protected]
Subject: Re: [NTSysADM] man-in-the-middle attack

 

Odds would be very difficult to extrapolate with any legitimate accuracy, as 
you need to know and control the possible environments and habits of your 
remote employees.  In any event, the odds are irrelevant - the issue is the 
business risk of intrusion/loss. 




--
Espi

 

 

On Wed, Jul 31, 2013 at 8:07 AM, David Lum <[email protected]> wrote:

  I need to present management with the odds of this actually getting 
exploited, as I’d want to force TLS 1.2 for ADFS but that takes Chrome and more 
importantly Safari (iOS devices) out of the mix, so I suspect management might 
say “we want compatibility instead of protection from some obscure attack that 
is unlikely to happen.

   

  In short, what are the odds of a MITM attack actually happening between my 
remote employee and our ADFS server?

  David Lum 
  Sr. Systems Engineer // NWEATM
  Office 503.548.5229 // Cell (voice/text) 503.267.9764

   

 

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