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I use Microsoft Outlook 2016 (abbreviated to O16) on my Windows 10 laptop that stores all emails offline, without Internet access. Canadian and US border agents are legally empowered to demand your password (See this and this): thus how can I legally preclude border agents from seeing my emails by clicking on O16?

  1. Using another computer for me is impossible, partly because uploading some documents online (e.g. to OneDrive or some online server) can threaten their security and privacy too.
  2. The only option that dawned on me, is to delete O16 entirely before crossing the border, and then reinstalling it after crossing successfully.
  3. Is there any other more efficient option?
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    There are various technical ways and means to hide emails and other data on your computer, which are probably better discussed on other SE sites. But you should be aware that you can be detained for a very long time for failing to comply with border security rules: this is not a question of outsmarting your average CBP officer. Your best solution is not to keep anything on your computer that you don't want other people to see. By the way, uninstalling Outlook does not necessarily remove the email archive from your user profile.
    – Calchas
    Mar 27, 2017 at 15:00
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    This belongs in superuser
    – JonathanReez ♦
    Mar 27, 2017 at 15:02
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    @JonathanReez I think it belongs in security.stackexchange.com myself, if we are going down a technical route, or perhaps law.stackexchange.com if we are going down a legal route.
    – Calchas
    Mar 27, 2017 at 15:03
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    You might find this post from a couple years ago (security SE) of interest. It has a link to an article by the Canadian Bar Association on preserving privacy. The best solution is to never have had anything of concern on the device. You can accomplish that with a notebook computer by imaging the drive when new and installing travel-only data and programs on a totally fresh drive. Or just use another computer.
    – Spehro Pefhany
    Mar 27, 2017 at 15:57
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    I'm voting to close this question as off-topic because it is either superuser or security SE.
    – user4188
    Mar 28, 2017 at 12:42

2 Answers 2

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This problem is encountered all the time by lawyers crossing the border, who are legally obliged to keep their communications confidential, but also face the prospect of having their laptops searched.

The solution almost always chosen is not to keep confidential information on the computer. Any contents you want protected is encrypted and backed up to a secure server, and then downloaded and decrypted once you are through the border. Innocuous documents, entertainment files and such can be left so as not to give a 'suspiciously clean' computer.

This post describes the situation in more detail (with thanks to Spehro Pefhany wro wrote this in a comment before me).

You can also keep the encrypted file on a memory device on your person. While border guards can search all your digital information in many jurisdictions, and can in some cases demand decryption passwords, anything that doesn't look like encrypted data is extremely likely to be allowed through (unless they already suspect you of something, in which case you are not likely to get through customs anyway).

It's also worth noting that the power to search devices is used extremely rarely.

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  • @SpehroPefhany I didn't see your link before writing this - if you wanted to write a post based on it, I would delete mine and vote yours up.
    – DJClayworth
    Mar 27, 2017 at 17:06
  • Your answer is a good one +1. It's worth noting that although it's indeed rare, the number is up more than 5:1 (23,887) in 2016 from the previous year .
    – Spehro Pefhany
    Mar 27, 2017 at 17:21
  • Having the device on you person doesn't matter one bit except that it may make discovery less likely. If they find it, they can decide to inspect it.
    – DTRT
    Mar 28, 2017 at 14:20
  • @Johns-305 Exactly my point. If you really don't want to store your files on a remote server (which seems to be the case with the OP) then a separate memory device is a way make them less likely to be discovered.
    – DJClayworth
    Mar 28, 2017 at 15:10
  • @DJClayworth Well, I wouldn't advise that. If it is discovered, it might look like a concealment which is even worse. Keep in mind, they're pretty thorough if they want to be.
    – DTRT
    Mar 28, 2017 at 15:50
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There are only two points to keep in mind:

  1. Everything is subject to inspection. Everything. To clarity, everything.*
  2. There is nothing you can say or do to prevent inspection if an Officer decides to inspect your belongings. Nothing. To clarify, nothing.*

If doesn't matter one bit if the material is illegal, confidential, sensitive, embarrassing, funny, disgusting or boring. If you can't risk border control seeing it, you cannot carry it across the border.

Keep in mind, CBP are full law enforcement officers and have a duty to protect information they come in contact with. Some confidentiality rules are defined here.

This really isn't that complicated. Think of your devices as you would you luggage, which is inspected all the time without objection.

The simple answer is, have nothing on your device or in you luggage that is illegal or you can't risk border control officers seeing.. CBP doesn't care if it's embarrassing, just illegal. An unmarked food can is very suspicious and Customs will likely demand you either open it or surrender it.

Many firms issue travel secured devices for exactly this purpose, to avoid complications at any border. All information is accessed online. But be aware that an unusually clean computer can raise questions on its own.

*A diplomatic pouch and Diplomatic Passport are one exception.

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    You seem to be assuming that if something is confidential, it must be either illegal or embarrassing. That's a huge assumption, there are literally hundreds of other possibilities. The asker could be anything from a celebrity's personal doctor to a lawyer on a high profile trial to an engineer working on a not-yet-patented invention or a PR person planning 2017's first big surprise release. Or even someone who's jealous ex works as a border guard. There are many possibilities that could be messed up badly by one overheard careless comment.
    – user56reinstatemonica8
    Mar 27, 2017 at 17:30
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    @user568458 I'm making no such assumption because it doesn't matter. Everything is subject to inspection. You can't claim the unmarked can is "confidential". If you don't want them seeing confidential material, you can't bring it across the border with you.
    – DTRT
    Mar 27, 2017 at 17:44
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    It's not just what is present 'on your device'. Your computer probably holds the keys to access confidential data on many other platforms- financial, legal, social media etc. Allowing random agents of foreign governments (or even your own government, but you may have more protections in that case) warrantless access to sensitive and highly private information is seldom a good option. They can inspect my keychain to make sure it isn't a knife, but not rifle through my home, business, car, and whatever else my keys may open. Not without a judge granting a warrant.
    – Spehro Pefhany
    Mar 27, 2017 at 18:43
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    @SpehroPefhany It still doesn't matter. Everything is subject to inspection. A pipe, while perfectly legal on most places, is an indicator for drugs. If you don't want them ruffling through your underwear, don't pack a pipe. There is no practical difference between your luggage and your laptop. If you can't risk border control seeing something, don't carry it across the border, anywhere.
    – DTRT
    Mar 27, 2017 at 21:53
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    @Johns-305 Your answer may be correct, but you have answered the wrong question. Assuming good faith on the part of the questioner, the question is not about hiding illegal materials. It is about the handling of sensitive and confidential materials in places where you cannot trust (or are not allowed to trust) border staff. I agree with the general principle of your answer (i.e., don't have have confidential information on your person) but I would politely disagree with the emphasis you put on illegal materials and with each of the parts that you have put in bold.
    – Calchas
    Mar 28, 2017 at 13:00