According to the CBC article quoted earlier, the border agents are only allowed to look at the information that is on your device and they are not allowed to download anything from the cloud without probable cause.
Aside from the customs issue, all of my files are in cloud accounts (I use OneDrive and iCloud, all encrypted). This allows me to access the files from anywhere and any device, keeping them up to date across all devices. Also, if a device happens to crash (or get confiscated for a long period of time), I can still access the files.
With that in mind, here is what I plan to do on my laptop, phone and iPad:
- Delete all email accounts, which removes all local emails. These are all easily added back after and the files will be downloaded from the server at that time.
- Log out of all cloud accounts and delete local files. Again, these are easily added back afterward and the files will be downloaded from the cloud.
- Clear all browsing history, and delete all cookies in any browsers on all devices.
- Logout of all social media accounts.
- Enable travel mode in 1Password.
I think the article said it best - you have to choose your battles. While I really have nothing to hide, the principle of an unwarranted search of my private information does not seem right to me. However, if the border agent asks for my passwords to any of my devices, cloud accounts, etc. I will probably comply. I will be crossing with my family of 5 and it will be easier to comply than risk a 2 week trip and the associated dollars spent on that trip. Although they are not "allowed" to do certain things, we all know that they can pretty much delay you for any reason.
I did contemplate backing up all of my devices, resetting them to factory before crossing and then restoring across the border. While entirely possible, this seemed like a bit of overkill. I also thought this could raise its own flags while crossing - again, choosing my battles.
That's my 2 cents. This works for me because I use the cloud, but it may not work for someone who stores all of their files locally on their devices.