What questions should we be asking ourselves before assigning digital work to students?

This is a brief post, for a couple of reasons. First, I am writing it on an iPad Air because I am tired of typing on my laptop. I just finished updating my manuscript for an upcoming ACSD Arias book regarding myths about technology. Second, during my research for the book I created a graphic regarding the question that serves as the title for this post. It didn't make the final cut, but I still think it is worth pondering. Here it is:

Hopefully the brevity of this post will allow for more comments and room for thinking. The topics of homework, adolescence, ubiquitous technology, and the kind of work we are asking students to do in today's always-connected world weigh on my mind.

Where do you weigh in?