I would not class a phishing attempt as a MitM attack; it’s just social 
engineering (or leveraging user ignorance) to obtain information. No one is 
getting in the middle at all; it’s just subterfuge. There are no technological 
solutions to behavior problems.
MitM is someone who has managed to interject his presence into a private 
conversation and eavesdrop on it (insert appropriate technical terms as needed 
to make the general definition more specific). It’s not a simple thing to do 
and that right there elevates the threat level. One does not go through the 
gyrations and work necessary for a successful MitM attack only to plant pop-up 
ads.

From: David Lum 
Sent: Thursday, August 01, 2013 9:43 AM
To: [email protected] 
Subject: RE: [NTSysADM] man-in-the-middle attack

Oh hey, maybe I should get caught up in the tread before replying…

 

·         Remote user goes to ADFS to leverage SSO to get to 3rd party for 
travel expenses, etc. which includes entering credit card data

·         Focus on MITM because the discussion became centered around TLS 1.2 
after I requested to turn off Extended Protection in IIS7 
(http://support.microsoft.com/kb/973917/en-us) which is only supported by IE

·         See bullet 1

 

What is the most common way to initiate a MITM attack? Phishing e-mail with a 
link?

 

Dave

 

From: [email protected] [mailto:[email protected]] On 
Behalf Of Andrew S. Baker
Sent: Thursday, August 01, 2013 6:43 AM
To: ntsysadm
Subject: Re: [NTSysADM] man-in-the-middle attack

 

I think you missed Ken's point, Micheal.

 

For any given scenario, the likelihood of it happening has to be considered AS 
WELL AS (not independently of) the consequences if it happens.

 

His last paragraph is instructive here:

 

    Using your method results in too much attention being paid to extreme 
events, and inadequate supervision of more mundane, even boring, events that 
result in small losses. Except lots of small losses can be just as crippling to 
a business.

 

 

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

 

I would respond that there is insufficient information in the thread thus far 
to actually answer that question.

 

David's question begs a few questions from me:

-- How are the ADFS servers being used as relates to these remote devices?

-- Why the focus on man-in-the-middle attacks?  (Is this the only perceived 
risk of remote and mobile systems?)

-- What apps will the users be accessing after authentication?

 

Regards,

 

      ASB
      http://XeeMe.com/AndrewBaker
      Providing Virtual CIO Services (IT Operations & Information Security) for 
the SMB market…
     

 

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