I have Roundup 0.8.1 installed on Windows 2003. 

In the roundup-server.ini, section:
[trackers]
TaskManager=C:\TaskManager\Roundup

In the config.ini, I have web=https://myhost/TaskManager/

this doesn't work! Roundup serves it up as
"taskmanager". Had to change the tracker web to
"https://myhost/taskmanager" (note captialisatioin) to
get it working.

Could the ConfigParser be at fault?