This started when I was having a problem with the printer connected via USB cable through my docking station. The Docked and Undocked hardware profiles where deleted and recreated at this time also but did not cure the issue. Resolution was to connect it via parallel cable and it would successfully undock. I had also re-imaged the laptop prior to me changing out the cable.
About a month or so after this, the problem of undocking the laptop with it displaying a black screen after undock started. I was shown how to properly undock the laptop prior to this so I don't believe that was the issue. Once again, the hardware profiles where recreated (both docked and undocked) that resolved the issue. Again, a month passed and the problem started again. This time I noticed that a Logitech Webcam software as well as Skype had been installed on the laptop. This is not to point a finger at that, just an observation. So I performed the same steps as before with recreated the hardware docked profile and undocked profile. It successfully undocked one time after this but when I redocked and attempted an undock again, same result. At this point since the laptop had already re-imaged two months prior, I decided to recreate my Windows XP profile after backing up everything on the laptop to a folder on my local C: drive called Backup. After rebuilding the profile (prior to setting up the dual screens) I was able to undock and redock the laptop successfully. At this time, I noticed that after setting up the dual screen configuration, the problem of not only not undocking would occur but it would not turn on the secondary monitor and I would have to do this manually when redocking it. So I logged on as myself to test and received the same results. It is using the most up to date video driver from Dell for the laptop as well. During this stage, the docking station was also switched out as well as removing the printer from the docking station.
At this point I'm at a loss as to where the problem lies. I'm leaning more towards the system not knowing how to address undocking with dual screens. Which brings me to a step that just occurred to me as to only use one primary 22" screen in the undocking process (many undocks and redocks) and not configure the secondary. This would point us to a source problem of the dual screens. Might need to go in this direction.. But that's the story thus far.