[liberationtech] was Secure hosted mail, now: VaultletSoft

[Jacob Appelbaum]

On 02/25/2012 10:06 AM, Robert Guerra wrote:
> John,
> 
> Autonomy Central (formerly called Vaultletsoft) is a secure hosted
> email solution that has not yet been mentioned on the list. It has
> several features not present in many of the other email solutions.
> 
> A couple of good things about Autonomy Central:  Several leading
> human Rights NGOs and donors have worked with and supported the tool
> over the last couple of years, and Source code - is - available for
> review.
> 
> https://www.vaultletsoft.com/ 
> https://www.vaultletsoft.com/about/source.html
> 
> Would be great to get people's comments on this..

I've met the author and he's a nice guy. However, I wouldn't suggest
that people use Vaultletsoft or Autonomy Central or whatever it is
called these days.

Some comments on why I'm not a fan:

It's not Free Software, it's not even Open Source software.

You have to use (!) their software to receive a copy of the source for
the software. That's a turtles all the way down security approach if
I've ever seen one!

To make matters worse anyone reading the source has to agree to some
license about peer review that includes this gem of a gag attempt:

"You agree that you will not post any information about any bug,
problem, deficiency, or weakness in the VaultletSuite Client software on
any web site or electronic bulletin board, or otherwise disclose or
provide any such information to anyone else, unless you have first
reported it to VaultletSoft Inc. and until at least 30 days after
VaultletSoft Inc. sends its email acknowledgement to you."

Getting into the actual tech - I find it rather concerning that many of
the VaultletSoft web services load a java applet to do the heavy lifting:
https://www.vaultletsoft.com/start/specialdelivery-popup-applet.html
https://production.vaultletsoft.com/vaultletsuite/vaultletmail/transomPopup.view

In a sense, I see two major problems. The first is a lack of open
standards in the crypto beyond the buzzwords of RSA and AES. The second
is that the security of the entire thing boils down to the security of
the SSL/TLS trust model. If every time you use the web forms you load
the java applets over TLS, a successful MITM wins the entire game. This
is not unlike the problems with Hushmail or in their case, I believe one
story was that they delivered a special java applet for a targeted user.
It's technically possible that the same thing could happen here, what
steps do they take to ensure that this doesn't happen?

As far as the client side software goes, I think that they solve
problems that need to be solved - I'm not sure that they solve them in a
way that makes sense. As an example I looked at the Vaultlet filer page
and noticed something quite strange:
https://www.vaultletsoft.com/products/vaultletfiler.html

Does it really disclose file names, contents, file sizes, and other
things *before* you provide an encryption key? That seems... uh, less
than ideal, if so.

As I absolutely refuse to audit something with a gag, I did not request
the source. I did however look at the portable linux installer and found
that it ships with a huge javakeystore. It appears that if each of these
CA certs is trusted that basically the TLS layer is vulnerable to attack
from each listed CA (Comodo is included in the list; DigiNotar isn't).
Though I won't make this claim, I've decided to CC the author and let
him reply here with a yes or no - if it's possible, I guess we'll call
that a pretty serious issue.

I've done a disassembly on the software as well but I don't have time to
look through it right now. I'll put it on the TODO list as it looks like
it might be an interesting target. The NDA/gag doesn't lend to the right
incentives thought and that really encourages me to audit some Free
Software projects when I do find the spare time.

All the best,
Jacob