Well, this broken behavior is relatively recent. I used to be able to sync content to my Pixel Slate all the time.
Indeed, it’s the entire reason that I got a Pixel Slate at all: I wanted to be able to sync content to the device for no-connectivity scenarios like plane flights, which I can’t do on my MacBook and other non-Android devices.
Since it worked before, and this seems like an unintended regression, do you think it’s likely to be investigated further?