Techniques are disclosed for automating the process of configuring a telephone system. More specifically, the techniques disclosed herein enable a telephone system to monitor the behavior of users of that system and to configure the users' preferences based on their observed behavior. For example, the system may observe that a particular user frequently dials a particular telephone number manually. In response to this observation, the system may automatically configure the frequently-dialed telephone number as a speed dial number for that user. As a result, the user may dial the number in the future by pressing a speed dial button rather than by entering the number manually. Such an automatic configuration process may enable the telephone system to be adapted to its users' needs more quickly and accurately, and with less effort on behalf of the users, than is possible using conventional systems that require their users to perform configuration manually.