[Andrex]

My question is whether the cost of creating and sending all these emails outweigh the Dropbox recidivism they induce.

Do these emails actually create value or is it a just way to make the company feel better about losing customers?

[sverhagen]

These emails are automated, so they can send them to many users, and only need a few to come back to make it profitable to do so. Also, the team that is responsible for these emails and for retention (or winning back defectors) may be its own little island and not care about contradicting the forever-promises made elsewhere in the business.