> If you deal with sensitive documents like legal artifacts in immigration cases, you want to have control over which of your documents wind up in the cloud and which you retain custody over.
This is incredibly easy with Dropbox or Google Drive. Everyone I know who uses these services has an intuitive knowledge for 'stuff in this folder goes in the cloud', and if they wanted to keep sensitive data off it they would know exactly how.
I am on an iPad, so no mature options for encrypting it myself with pgp or something really exist. I shouldn't upload it to a cloud service (although chances are that it already is, because pretty much every iOS app uses a cloud of some sort). I shouldn't email it. I can't plug in a physical usb device because iOS doesn't have File reading access to. I guess I convince everyone to use Signal? That is pretty impractical for 'normal' people to convert everyone over to their own messaging app.
Also, on your phone, what browser do you use? Chrome? Well, not really because it is all webkit under the hood, so you are going to be using Safari no matter what.