Thanks Moonchilde for the suggestion, however I did already have the folders in place and was even copying other shortcuts into those same folders. The good news is that I have figured out the issue. Once the unattended installer finished (and once again didn't copy the shortcuts to the appropriate places) I navigated to the directory using command prompt (C:\ProgramData\Microsoft\Windows\Start Menu\Programs) and noticed that the two shortcuts I was trying to move (Windows Media Player.lnk and Desktop Gadget Gallery.lnk) didn't exist, even though they are clearly visible at the top of the start menu, and appear when you navigate to that folder in Explorer. In the command prompt window I looked through the files that were listed and noticed that there were two there that didn't show up in the Start Menu: sidebar.lnk and media center.lnk . So those are the two files I need to move, but somehow they have a different name! This is new to me, but maybe some of you have seen it before? Strange...but thanks to you guys who tried to help. It was appreciated! If you check the links in the start menu on an actual install, they actually point to %windir%\ehome\ehshell.exe (for media center) and "%ProgramFiles%\Windows Sidebar\sidebar.exe" /showgadgets for the gadget gallery. Try editing those instead, and maybe just using the delete command. Or, you could just do what I mentioned earlier. Mount your WIM image and then just edit the directories you want instead of using the batch to move stuff during install. The install will simply copy over the edited wim file with the start menu stuff all set up as you want.