As of Sept 30 2013, Xabber added Orbot support. This is a huge win for chat security. (Gibberbot has done this for a long time, but it isn’t as user-friendly or pretty as Xabber and it is hard to convince people to use it).
The combination of Xabber and Orbot solves the three most critical problems in chat privacy: obscuring what you say via message encryption, obscuring who you’re talking to via transport encryption, and obscuring what servers to subpoena for at least the last information by onion routing. OTR solves the first and Tor fixes the last two (SSL solves the middle one too, though Tor has a fairly secure SSL ciphersuite, who knows what that random SSL-enabled chat server uses – “none?”)
There’s a fly in the ointment of all this crypto: we’ve recently learned a few entirely predictable (and predicted) things about how communications are monitored:
1) All communications are captured and stored indefinitely. Nothing is ephemeral; neither a phone conversation nor an email, nor the web sites you visit. It is all stored and indexed should somebody sometime in the future decide that your actions are immoral or illegal or insidious or insufficiently respectful this record may be used to prove your guilt or otherwise tag you for punishment; who knows what clever future algorithms will be used in concert with big data and cloud services to identify and segregate the optimal scapegoat population for whatever political crises is thus most expediently deflected. Therefore, when you encrypt a conversation it has to be safe not just against current cryptanalytic attacks, but against those that might emerge before the sins of the present are sufficiently in the past to exceed the limitations of whatever entity is enforcing whatever rules. A lifetime is probably a safe bet. YMMV.
2) Those that specialize in snooping at the national scale have tools that aren’t available to the academic community and there are cryptanalytic attacks of unknown efficacy against some or all of the current cryptographic protocols. I heard someone who should know better poo poo the idea that the NSA might have better cryptographers than the commercial world because the commercial world pays better, as if the obsessive brilliance that defines a world-class cryptographer is motivated by remuneration. Not.
But you can still do better than nothing while understanding that a vulnerability to the NSA isn’t likely to be an issue for many, though if PRISM access is already being disseminated downstream to the DEA, it is only a matter of time before politically affiliated hate groups are trolling emails looking for evidence of moral turpitude with which to tar the unfaithful. Any complacency that might be engendered by not being a terrorist may be short lived. Enjoy it while it lasts.
And thus (assuming you have an Android device) you can download Xabber and Orbot. Xabber supports real OTR, not the fake-we-stole-your-acronym-for-our-marketing-good-luck-suing-us “OTR” that Google hugger-muggers and carom–shotts you into believing your chats are ephemeral with (of course they and all their intelligence and commercial data mining partners store your chats, they just make it harder for your SO to read your flirty transgressions). Real OTR is a fairly strong, cryptographically secured protocol that transparently and securely negotiates a cryptographic key to secure each chat, which you never know and which is lost forever when the chat is over. There’s no open community way to recover your chat (that is, the NSA might be able to but we can’t). Sure, your chat partner can screen shot or copy-pasta the chat, but if you trust the person you’re chatting with and you aren’t a target of the NSA or DEA, your chat is probably secure.
But there’s still a flaw. You’re probably using Google. So anyone can just go to Google and ask them who you were chatting with, for how long, and about how many words you exchanged. The content is lost, but there’s a lot of meta-data there to play with.
So don’t use gchat if you care about that. It isn’t that hard to set up a chat server.
But maybe you’re a little concerned that your ISP not know who you’re chatting with. Given that your ISP (at the local or national level) might have a bluecoat device and could easily be man-in-the-middling every user on their network simultaneously, you might have reason to doubt Google’s SSL connection. While OTR still protects the content of your chat, an inexpensive bluecoat device renders the meta information visible to whoever along your coms path has bought one. This is where Tor comes in. While Google will still know (you’re still using Google even after they lied to you about PRISM and said, in court, that nobody using Gmail has any reasonable expectation of privacy?) your ISP (commercial or national) is going to have a very hard time figuring out that you’re even talking to Google, let alone with whom. Even the fact that you’re using chat is obscured.
I’m using an Ubuntu VM for private browsing, and like many people, I’m stuck using a mainstream OS for much of my work (Win7) due to software availability constraints. But some software works much better in a linux environment and Ubuntu is as pretty as OSX, free, and installs easily on generic x86 hardware.
It is also pretty straightforward to install an isolated and secure browsing instance using VirtualBox. It takes about 20G of hard disk and will use up at least 512K (better 1G) of your system RAM. If you want to run this sort of config, your laptop should have more than enough disk space and RAM to support the extra load without bogging, but it is a very solid solution.
Installing Ubuntu is easy – even easier with an application like VirtualBox – just install virtualbox, download the latest ubuntu ISO, and install from there. If you’re on bare metal, the easiest thing to do is burn a CD and install off that.
Ubuntu desktop comes with Firefox in the tool bar. Customizing for private browsing is a bit more involved.
My first steps are to install:
- noscript to create your own whitelist of sites allowed to run scripts,
- better privacy to apply rules for deleting flash cookies,
- TACO to control tracking cookies,
- UserAgentSwitcher to make your ubuntu/firefox rig generic looking,
- Tor Button to browse without leaving a trail of your IP address.
NoScript is an easy win. It is a bit of a pain to set up at first, but soon you add exceptions for all your favorite sites and while that isn’t great security practice, it is essential for sane browsing. NoScript is particularly helpful when browsing the wacky parts of the net and not getting exotic browsing diseases: it is your default dental dam. Be careful of allowing domains you don’t recognize – Google them first and make sure you understand why they need to run a script on your computer and that it is safe. A lot of sites use partners for things like video feeds, so if some function seems broken, you probably need to allow that particular domain. On the other hand, most of the off-site scripts are tracking or stats and you really don’t need to play along with them.
BetterPrivacy is a new one for me. I am very impressed that it found approximately 1.3 zillion (OK 266) different company flash cookies AFTER I had installed TACO and noscript etc. You bastards. I’m sure I can enjoy hulu without making my play history shared-available to every flash site I might visit. Always Sunny in Philadelphia marks me as a miscreant. I flush the flash cookies on starting silently (preferences).
TACO is a bit intrusive, but it seems to work to selectively block tracking and advertising cookies. At least the pop up is comforting. For private browsing, I’d set it to reject all classes of tracking cookies (change the preferences from default).
User Agent Switcher is useful when you’re deviating from the mainstream. Running Ubuntu pretty much flags you as a trouble maker or at least a dissident. Firefox maybe a bit less so, but you are indicating to advertisers that you don’t respect the expertise of those people far smarter than you who pre-installed IE (or Safari) to make your life easier. Set your user agent to IE 8 because the nail that sticks up gets pounded down.
Torbutton needs Tor to work. Tor provides really good privacy, but is a bit involved. The Tor Button Plugin for firefox makes it seem easier than it really is: you install it and click “use tor” and it looks like it is working but the first site you visit you get an proxy error because Tor isn’t actually running (DOH!).
To get Tor to work, you will have to open a terminal and do some command line fu before it will actually let you browse. Tor is also easier to install on Ubuntu than on Windows (at least for me, but as my browser history indicates I’m a bit of a miscreant dissident, so your mileage may vary).
Starting with these fine instructions.
sudu gedit /etc/apt/sources.list
deb http://deb.torproject.org/torproject.org lucid main
deb-src http://deb.torproject.org/torproject.org lucid main
gpg --keyserver keys.gnupg.net --recv 886DDD89
gpg --export A3C4F0F979CAA22CDBA8F512EE8CBC9E886DDD89 | sudo apt-key add -
sudo apt-get update
sudo apt-get upgrade
sudo apt-get update
sudo apt-get install tor tor-geoipdb
Install vidalia with the graphical ubuntu software center or with
sudo apt-get install vidalia
Tor expects Polipo. And vidalia makes launching and checking on Tor easier, so remove the startup scripts. (If Tor is running and you try to start it from vidalia, you get an uninformative error, vidalia has a “launch at startup” option, so let it run things.) Vidalia appears under the Applications->Network.
sudo update-rc.d -f tor remove
Polipo was installed with Tor, so configure it:
sudo gedit /etc/polipo/config
Clear the file (ctrl-a, delete)
paste in the contents of this file:
(if the link above fails, search for “polipo.conf” to find the latest version)
I added the binary for polipo in Vidalia’s control panel, but that may be redundant (it lives in /usr/bin/polipo).
I had to reboot to get everything started.
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