In order to do this you need a windows macro like autohotkey and IBController (http://sourceforge.net/projects/ibcontroller/). This is assuming that you do not have a security key on your IB account. If so this cannot be completely automated. You would still need to be present to enter the key. edit: You may not need the windows macro after I think about it for a minute though. this is only necessary if there are GUI controls involved. You can probably get away with starting IBController through a .bat file or desktop shortcut and then scheduling it to run as a task. Autohotkey is very useful for automating other tasks in Windows though.