The Rise of the “Traveltop”

A paranoid guide to traveling with a laptop computer.

I don’t travel much for work, but I do get around for vacation or conferences. I have traveled internationally a couple of times in the last year, and around the U.S. several times. This is how I approach laptop security when I am traveling.

A big concern to many people is what you keep on your laptop. My personal laptop has information that I don’t wanted shared, and my work laptop has information my employer doesn’t want shared. A few concerns when traveling are laptop theft, search and seizure by a friendly three letter government agency (who, rest assured, have your best interests in mind,) evil-twin hotspots, and traffic interception.

There are a few ways to deal with each problem, which are helpful for travelers. The first rule is to anticipate that the worst will happen: your laptop will be stolen, searched, attacked, or sniffed at some point.

The best protection is to use what I like to call a “traveltop”, which is a laptop configured solely for traveling. The key should be that you are willing to walk away from the laptop and not give it a second thought. There are plenty of laptops available for less than $500. I am not talking about something like an EEPC or watered down laptop, I picked up a Toshiba Satellite for roughly $450, which has 64bit dual core AMD processors and is sufficiently fast for almost everything I could want to do outside of gaming. My Macbook Pro cost me more than five times as much. Think of it as cheap insurance.

The key for this strategy to be effective is to limit what information you put on the laptop. Don’t use it for creating and editing documents, don’t store email on it, don’t even put your web bookmarks on it. Here are some of the methods I use to keep my traveltop clean, likely to resist attack, and divulge the minimum information to someone who gets their hands on it:

1. Buy a throwaway. If you are traveling with any frequency it is likely that you make enough money to afford a $450 laptop. If you can’t afford that, maybe you should reconsider taking a computer at all–if you can’t afford to lose your laptop leave it at home and use a phone for checking email.
2. Use Firefox. Don’t use Internet Explorer. Configure Firefox to delete all cookies, history files–everything when you close it. You can do this by clicking on Tools -> Options -> Privacy, and clicking the checkbox that says “Always clear my private data when I close Firefox.” I realize this doesn’t protect you from a full forensic analysis, but it does help limit your exposure. For example the TSA will check your Internet history when looking at a suspect laptop.
3. Install Google Toolbar. I know, it sounds counter-intuitive, but the only thing I use from the Google toolbar is the feature that allows you to share bookmarks across different systems. Not only is it convenient–but it is safer because your bookmarks are stored online and require authentication to access them. Don’t get a false sense of security though, because google will leak your session cookie unencrypted, which allows anyone sniffing the network you are on to login as you while the cookie is valid–this is easily dealt with, and is covered later.
4. Use webmail. Google is good, hushmail is safer–which ever one you choose don’t store your messages on your traveltop, don’t even print them from the traveltop–in fact I highly suggest not even configuring a printer on the system.
5. Encrypt the entire hard drive. Truecrypt is free, faster than most commercial alternatives, easy to install, and runs on most popular operating systems (Windows, Mac, and Linux.) I suggest using a really long password–actually don’t use a password, instead use a sentance it will be easier to remember, and will stand up a lot better to automated key guessing. A couple of thoughts about dealing with government agencies (foreign or domestic.) If a border agent demands your password, or requests that you type it–comply. There is no reason to go to jail, and unless you are well funded and plan on taking on the courts (and it would require an incredibly large effort) you will lose. Although Truecrypt has the ability to have “hidden” partitions with entire operating systems inside of them–with so called “plausible deniability” this is in my opinion a bad idea. First, some research has shown that it is possible to detect (under certain circumstances) that this is being used. Second, if you get caught deceiving police, border agents, whatever you can get into a lot more trouble–it may establish mens rea. But, IANAL–don’t trust me for legal advice :)
6. Don’t save documents locally. If you must carry documents use an encrypted thumb drive to store them. Send the thumb drive to yourself at your destination using registered mail. Better yet, if you can use a web-based solution such as Webdav, or Google Documents use that. Another good solution is to use something like a Remote Desktop or Citrix session to access your files–which almost completely eliminates the likelihood that you will inadvertently place something secret on on your traveltop.
7. Use an encrypting proxy for Internet traffic. If someone is going to watch your network traffic it will most likely happen at a wireless hotspot. Many times programs leak information that an attacker can use even if the login is encrypted, a good example of this is Google Mail, which allows cookie theft. One method of dealing with this is to use an encrypted tunnel to a trusted (or more trusted) network. There are free and commercial products for doing this. If you don’t have any technical expertise, one method is to use Anonymizer a commercial web service that helps Windows users. More technical users may want to use a SSH Tunnel or setup a proxy server such as Squid or Apache using SSL and authentication. By verifying the SSL encryption certificate (or SSH key) you can be sure that no one has performed a man in the middle attack, or is injecting data as is common in evil-twin attacks.
8. Clean house frequently. You should use a program that cleans up tracks of web surfing, temporary files, and other day to day activities.  Webroot software makes Window washer, which works reasonably well, but is a little flaky under UAC on VIsta.  Anonymizer makes a competing product that is bundled with their web surfing tool, but they have problems with Firefox 3.  A feature that is desirable is the ability to “wipe” files and not just delete them (if you can turn this on permanently for your Recycle Bin it is better.)  Wiping the file with random data before renaming it and then removing it makes it effectively impossible for the deleted file to be recovered, even partially.
9. Use a firewall, anti-virus and anti-spyware software. This is a no-brainer. I am, however, skeptical about expensive programs. Use the free stuff like Avira, and the free Windows anti-spyware stuff. Don’t open strange attachments, don’t run as the administrator user, and don’t use your traveltop to surf pr0n! I know a lot of people say that Vista is not ready for prime time, but for most users it provides protection that XP lacks.
10. Update your software. Yes, I know, this is another no-brainer. A day or two before you leave for your trip you should use Windows update to get current. Stay on the latest version of your web browser too. Why does this matter? Many evil-twins will attempt to exploit your system by attacking known security weaknesses that have already been fixed. For an example of such a program, check out Hotspotter–it is particularly devious, and having the latest system updates installed really helps protect your system.
11. Buy a laptop lock, and use it when you leave your laptop alone. Sure a few blows with a hammer will break most laptop locks, and many are easy to pick. What you are trying to stop is crimes of opportunity. If someone is targeting you for theft they are more likely to be successful, but most thefts aren’t planned and most of the lock picking enthusiasts aren’t thieves. So buy a lock and use it.
12. Use an anonymous recovery service. I put little stickers on all my expensive electronics, that offer a reward through Track it Back, which is a service that offers a reward to people that find your belongings, and arranges to have a courier pick it up and mail it back to you. There are other services out there too. Basically it assumes that many people are honest, and will return something of value that they find. The allure of a reward may be more tempting for a thief that discovers that your laptop won’t boot without a password.
13. Make your laptop less attractive. I put stickers all over my traveltop–it makes it distinct, harder to claim “Oh, it looks just like mine, sorry”, and destroys the resale value for a thief.

The most important concept is that by not placing valuable information on your laptop you don’t put it at risk. I know it seems obvious, because it is, but how many big corporations have you heard about this year alone that lost something of value?