Can it happen? Of course. You can't figure out user satisfaction with certainty until you show them the goods. One of the fundamentals of Agile development. The thing is, lots of developers have trouble with two important ingredients: listening and preparing.
- Listening: Rather than the narrow definition (using ears only) I also use that for 'reading carefully', and 'paying attention to signs'. Not only handling every detail, but also trying to understand why the user has come up with something. In e-mails, first of all make sure you react to everything brought up by the user. The 'old style' e-mail response works really well (interleaved quoting and answers). But good listening is much more than that.
- Preparing: Agile requires lots of interaction with users. On the other hand, lots of user interaction is simply unnecessary. Not just because you could have figured it out yourself. Very often it's harmful. There are many things in life that need preparation, and sure as hell interaction with users needs careful preparation. I can think of hardly any case where I just go over to the users and start like 'please tell me what you want'. Do they know? They may think they do. Do you know what you have to offer? Probably not. Investigate.