The first weeks and months of any 1:1 pilot are difficult. Facing each new learning obstacle with a new device seems awkward, ungainly, and not part of the normal planning process. There WILL be a moment when using technology to solve a problem actually becomes the problem itself. For example, the first time that I used dropitto.me, I failed to realize the importance of a standard naming convention. As a result, ⅓ of the students assignments were lost. Oops!