Config keys are not introspectable
CherryPy has recently been touted as [http://blog.dowski.com/2006/03/05/cherrypy-and-the-interactive-interpreter/ easy to mess around with from within the interactive interpreter]. This is a direct side-effect of CherryPy's re-use of existing Python idioms for startup and shutdown, handler dispatch, redirection, etc.
One facet of CherryPy which does not follow this "Pythonic" design style is the config module. Configs are stored in a flat dictionary, and re-invent (in a very limited way) the object heirarchy via "component.setting" syntax in strings. Since these config entries may simply not be present, they are not introspectable, and require the poor user to rely either on perfect docs (which are not CP's strong point yet), or on reading the source code. This is a significant barrier to entry for new users, and even for experienced users who are exploring any functionality which they have not used before.
This could be remedied by separating the OO configuration settings from the "logic which parses configs declared in a file". That is, rather than make the settings behave like a config file, they should be declared and behave in a more expressive, object-oriented style; CP would then provide a tool to transform/apply a configfile to that.