So Twitter has two modes of retweeting: with or without comment. They decided to implement this with an additional popup dialog. It sort of works, but adds unnecessary step which makes the process harder that it should be for both cases.
What they could’ve done instead is making two separate buttons, quick retweet and retweet with comment. This way quick retweet would be, well, quick, and retweet with comment would ask for a comment. Instead of asking for directions later, just make two quick shortcuts and everybody would be happy.