In the past I rolled out software by manually installing it on a "golden" workstation, creating an (ghost)image from that and rolling that out to the other workstations.

I try not to do that any more for simple/small software, and when possible (if it's an .msi) I assign the software through gpo. I'm having a problem with one of those.

The software was manually installed on the image, which was rolled out, and now I have an update for that software (new msi) and I'd like to assign it through gpo. Don't know if it's relevant but it's user assigned.

The new version gets installed alongside with the old version (this is possible since the program folder is different between those versions). When I install the same msi by hand, it properly removes/upgrades the old version though. Is what I am trying to do possible?