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Dear FDE list:

I'm starting to get involved in an encryption project and have some
thoughts about Windows-based encryption tools...I've used TrueCrypt, PGP
and GPG for years, but usually only in single-user mode and haven't had
to concern myself with key-escrow, enterprise backup, imaging, policies,
and other details.

I'm concerned about data protection against unauthorized people and
against malware, mostly on desktop and laptop Windows boxen.

If data is to be protected when the system is powered down, FDE makes a
lot of sense. If the system is at risk for theft/bootdisk drive access,
FDE makes a lot of sense.

If data is to be protected when it's only accessed occasionally, then
file/folder encryption makes sense.

If the data to be protected must be accessed on a continuous basis, what
are some strategies that can be used, given the reality of 0day and the
modern threat landscape? Head back to pen & paper?

There are a few concerns that I have; these may be in some FAQ (pointers
appreciated!)

How do you handle persistent temp files on Windows boxes such as those
generated by MS-Office? Sure, they are protected by FDE when the box is
powered down. but what about when the user has decrypted/booted past the
FDE auth and then gets nailed by a 0day in some client application?
(please don't say "just don't get owned") Hope and pray that they
weren't running as Administrator? Have them pull the network plug and
hope that the undetected keylogger they have doesn't just cache
everything for delivery the next time an Internet connection is
available? And those scenarios are just when you *know* that an attack
has taken place.

The current state of Windows malware as I understand it is that the user
must generally be running as Administrator (for client-side malware;
obviously server components running as LocalSystem with bugs that open
ports are still a risk) in order for most malware to be able to do it's
nastiness. If someone is a restricted user then most malware will
probably fail, unless it's designed to do privilege escalation tricks or
unless it's designed to snag *data* that this particular user has access
to (decrypted, if using FDE and the system is booted, or decrypted if it
was protected with file/folder encryption and the user had need of that
data, or kept the data open longer than needed). I expect in the future
to see malware that does things like leverage priv escalation attacks,
and implement a sensitive data search to look for SSN's on the box
accessible to the logged-in user, pack them up with a key of the
attackers choice and HTTP upload those to the attackers malicious
server. Maybe this is already happening.

I'm aware of the usual protection techniques such as hardening,
anti-<malware,virus,spyware,scumware,trojan,rootkit...> etc. but what I
am interested in learning is how to best approach an encryption scenario
in the face of such contemporary threats. Perhaps my expectations are
too high.

I think that one must have FDE and file and folder encryption at the
same time to really cover things, but depending upon the usage scenario
f&f might not be helpful. I am not yet well-informed on the various
vendor offerings and would appreciate any suggestions, on or off-list.

Thank you

GnuPG key: http://www.infotech.siu.edu/security/curtw.pub.asc

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