We need a constitutional amendment that says "we really mean it" with respect to the 4th and 9th amendments, explicitly including personal digital data and criminalizing general surveillance. With fangs.

We really need a concept of tenancy in a digital context.

Your personal papers are perfectly safe and subject the fourth amendment protections in your rented apartment. But most digital materials are considered to have been shared with a third-party if you store them on Google Drive.

My feeling about this stuff personally is that the biggest issue is that stuff that happens in electronic devices is different in a modern sense than what anyone intended in the past. If you could figure out a way to make my personal property as it exists on a foam or another device, the same as the personal property that’s in my desk at home or the trunk of my car then technology would be able to solve a lot of these problems. I think the custom thing is a more nuance conversation. I don’t understand the theory of it enough, but intuitively it seems ridiculous that a CBP officer has the ability to legally go through 30 years of my pictures in my Apple album because I happen to be crossing a border.

The border search exception was designed by the framers.