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Re: Security of Mac Keychain, Filevault

daemon@ATHENA.MIT.EDU (Jerry Leichter)
Mon Nov 2 22:02:47 2009

Cc: Cryptography List <cryptography@metzdowd.com>,
 Steven Bellovin <smb@cs.columbia.edu>
From: Jerry Leichter <leichter@lrw.com>
To: "Jeffrey I. Schiller" <jis@mit.edu>
In-Reply-To: <3012355.1111257201367638.JavaMail.root@dune1>
Date: Mon, 2 Nov 2009 20:41:04 -0500

On Nov 2, 2009, at 5:36 PM, Jeffrey I. Schiller wrote:

> ----- "Jerry Leichter" <leichter@lrw.com> wrote:
>> for iPhone's and iPod Touches, which are regularly used to hold
>> passwords (for mail, at the least).
>
> I would not (do not) trust the iPhone (or iPod Touch) to protect a
> high value password.
There are two problems with this:  So many of the things you'd really =20=

like to be able to do with your iPhone/Touch/other smart phone require =20=

a key whose value is very difficult to calculate (e.g., just what =20
would you lose if someone could read all your mail?); and services =20
increasing bundle all kinds of things together under one password.  =20
For example, all your Google services use the same password; and your =20=

Apple Mobile Me mail password is also the key to such things as you =20
contact list (if you sync it) and Back To My Mac (which I now disable, =20=

useful as it might be, for just this reason) and your iTunes store =20
account.  You can dissociate some of these, directly or indirectly, =20
but the services assume they are tied together and don't work nearly =20
as well if you do that.  The trend is for this to get worse, with =20
network-wide shared authentication via OpenID or whatever other =20
standard catches on.

> Or more to the point I would change any such
> password if my iPhone went unaccounted for.
Oh, absolutely.

> In the case of the Mac Keychain and Filevault, if implemented
> correctly, the security hinges on a secret that you know.
And you know this ... how?  Have you, or anyone you know, vetted the =20
design?  Sure, *if* it's all implemented correctly, it maintains =20
*some* set of security properties.  Do you even know what those are?  =20=

I know I don't....

> Pick a good
> secret (high entropy) and you are good. Pick a poor one, well...
>
> However the iPhone=92s keychain is not encrypted in a password. =
Instead
> it is encrypted in a key derived from the hardware. The iPhone
> Dev-Team, the folks who regularly jail break the iPhone, seem to have
> little problem deriving keys from the phone! Note: Setting a phone
> lock password doesn=92t prevent me from accessing the phone using the
> various jail breaking tools. Presumably once I have control of the
> phone, I have access to any of the keys on it.
That would be my assumption, too.

As the value of the information in smartphones grows daily, their =20
vulnerabilities will be more and more of a problem.  Remote wipe - =20
assuming it really destroys the data - helps against loss, but does =20
nothing against a deliberate, targeted attack, which can probably copy =20=

all the data within minutes.  We need some new thinking here.  One =20
possible approach, based on an idea IBM played with a couple of years =20=

back but that as far as I know never made it into a product:  Build a =20=

Bluetooth-connected ring or key fob that must be physically quite =20
close to the device to keep it unlocked.  IBM did this for laptops, =20
and just locked the screen.  For a smartphone, you'd want the phone =20
and the fob to mutually authenticate, and then the fob would transfer =20=

a key that could be used to unlock critical data on the phone.  When =20
the fob goes out of range, the phone wipes the key and all decrypted =20
data.  One can certainly come up with attacks on this - even so simple =20=

as the smart mugger scenario:  Give me your phone and your fob - but =20
it raises the bar, with minimal inconvenience in normal use.
                                                         -- Jerry

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