Speech-based applications commonly come with web-based or printed manuals. Alternatively, the dialogue can be designed so that users should be able to start using the application on their own. We studied an alternative approach, an integrated tutor. The tutor participates in the interaction when new users learn to use a speech-based system. It teaches the users how to operate the system and monitors user actions to be certain that the users do indeed learn. In this paper we describe our experiences with the design and the iterative development of an integrated tutor. Expert evaluation and two user tests were conducted with different versions of the tutor. The results show that the tutor can effectively guide new users. We identify the six most important lessons learned, the most important being that it is essential to spot problems by monitoring user actions, especially when novice users are tutored. Categories and Subject Descriptors: H.5.2 [User Interfaces]: Voice I/O, Natural langu...