Communication is about people, not machines. But as firms and families alike spread out geographically, we rely increasingly on telecommunications tools to keep us “connected”. The challenge of such systems is to enable conversation between individuals without computational infrastructure getting in the way. This paper compares two speech-based communication systems, Phoneshell and Chatter, in how they deal with the keys to communication: proper names. Chatter, a conversational system using speech-recognition, improves upon the hierarchical nature of the touch-tone based Phoneshell by maintaining context and enabling use of anaphora. Proper names can present particular problems for speech recognizers, so an interface algorithm for reliable name specification by spelling is offered. Since individual letter recognition is non-robust, Chatter implicitly disambiguates strings of letters based on context. We hypothesize that the right interface can make faulty speech recognition as usable as TouchTones—even more so.