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Re: auditing web/mail proxies
From: Justin Rogosky <jrogosky () gmail com>
Date: Tue, 6 Dec 2011 14:42:12 -0500

To sum up what Anders said (feel free to correct me if I am wrong), it
all depends on what you are trying to prove.
If you want to prove that you can exfiltrate data, then try sending
something marked up to be confidential (this comes in a variety of
marking and classification that is hard to be specific).
In addition, there is a BIG difference between pen testing and
auditing, so depending on if it is a pen test or audit your goals will
be wildly different.

If you are auditing, look at the settings of the system.  See if they
are whitelisting or blacklisting.  Is SSL being intercepted?  Is DNS
part of it in that they are resolving IPs to determine accessibility?
What key words are they hitting on to prevent data leakage.  It is a
long list of things to check and depends on scope of the test.


On Tue, Dec 6, 2011 at 2:36 AM, Anders Thulin <anders.thulin () sentor se> wrote:
On 2011-12-05 10:21, cribbar wrote:

Has anyone ever audited a proxy during a pen test/IT audit or as an audit on
itself? If so do you have a scope of what kind of checks you reviewed, or a

 An audit is intended to answer the question: does the examined system work
according to the rules and regulations it should follow? The next question is,
obviously, are there any such rules?

 That should be answered by the organization owning or otherwise managing
the proxy: what rules should be followed? These will typically relate to the
management of the proxy: how is access controlled, how are changes implemented,
how are logs and backups handled, and so on. (Tests of proper function -- quality
testing -- is usually not regarded as part of an audit. That's more akin to
penetration testing.)  The rules need not be expressed for the proxy specifically,
they could be part of an IS or IT policy, applying to all IS or IT systems in
the organization. And in some special cases, they might even take the form of
local or national law.

 For an audit, you job includes defining the system you are auditing (the word
'system' is used an a fairly general sense here -- it needn't be just a network 'box',
but an entire proxy support and management -- don't forget helpdesk!), identify
the rules that are relevant that system, and then verify that they are indeed being

 If there are no relevant rules, an audit cannot be done.  If the system cannot
be strictly defined (in the sense of if some entity is part of the system or not),
there will be difficulties later. Additionally, if there are rules, but they cannot be
audited (quite often because they are imprecise), the only thing is to identify the
problem, and suggest a remedy for the next audit.

 There *are* usually best practice suggestions, which, in the absence of other
requirements, could (barely) be used. But again, the system definition decides:
are you looking at a proxy box only, or a component in a network, at a system
that must be managed over it's lifetime, alone or in relation to other information systems
of which it is considered a part?

 'Muscular audits' ... deciding on your own what the rules are (or should be) is a
possible way, technically, but it's so far from the accepted definition of an audit that
I don't consider it practical.

Anders Thulin      anders.thulin () sentor se      070-757 36 10 / Intl. +46 70 757 36 10

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