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Technologically, encryption is imperfect because even strong crypto can be cracked when someone obtains the keys. Border agents can demand the keys from travelers unwilling to face seizure or detention. Agents may also be able to extract and use keys that are stored on the machine itself. Generally, if you keep your keys with the laptop, in your head or on your disk, then the encryption is easier to socially engineer or break than if you keep the keys elsewhere. (Discussion of what encryption techniques to use or avoid is beyond the scope of this post.)
"Encryption aside, there may be other ways you can show CBP that your laptop is indeed a normal computer and that you mean no harm while keeping confidential information from prying eyes. Most operating systems let users to create multiple accounts on a single machine. A traveler could allow CBP to examine his own account, while storing client data or trade secrets in a separate account “owned” by his law firm or corporation. Under typical border search circumstances, this might satisfy CBP concerns. However, simply storing information in a different account—even one protected by a password—is not the same as encrypting it. If CBP is interested, the most commonly used forensic search tools can access and search non-encrypted data in every account on the machine.
"Law firms, corporations and other entities that routinely deal with confidential information are handing their business travelers forensically clean laptops loaded with only what the traveler needs for that particular business trip. Leaving unnecessary data, like five years of email, behind may be the best thing. Of course, if trade secrets or client information are the reason for the trip, this plan will not help.
"Another option is to bring a clean laptop and get the information you need over the internet once you arrive at your destination, send your work product back, and then delete the data before returning to the United States. Historically, the Foreign Intelligence Surveillance Act (FISA) generally prohibited warrantless interception of this information exchange. However, the Protect America Act amended FISA so that surveillance of people reasonably believed to be located outside the United States no longer requires a warrant. Your email or telnet session can now be intercepted without a warrant. If all you are concerned about is keeping border agents from rummaging through your revealing vacation photos, you may not care. If you are dealing with trade secrets or confidential client data, an encrypted VPN is a better solution.
Finally, however useful these techniques might be to protect laptops, travelers do not have this array of options for protecting data stored on less configurable smart phones. Of course, many phones do have a lock or password protection option, which travelers might consider enabling before heading to the airport....