@mcrudd I know this is an old thread, but I found it while looking to solve my own issue with desks. It didn't help me, but what I did find, and hopefully this will help someone else looking for a resolution, was that sometimes it's something to do with your build. Some spots you try to place desk and chair just don't work because something else is in the way, even though it's not obvious. That's what my problem turned out to be. I tested desks and chairs on another lot/neighborhood that had already been placed, placed new ones there etc., and it all worked. So I went back to the neighborhood I was working on and messed around with a desk and chair combo I knew worked, and just moving to a different spot fixed the problem. Sometimes it's windows, doors or other things that are just too close, other times I still haven't figured out why, but at least I know it's not the desks and chairs. Hope this helps someone who stumbles across this same issue.