Thanks for confirming, Keith. I decided to go and do more testing, and this time, I think I figured it out. It was only when a token was assigned and had sight that it began ignoring the commands. I started with two unassigned tokens like you did. I can move them front and back with no problem. When they are both assigned to me, I can do the same. When they are both assigned to me, but one of them has sight and the other does not, the one with sight always stays on top. When I give them both sight (and they are both assigned to me), I can also switch them back and forth freely. Finally, when I tested them both unassigned but one had sight and one didn't, I could freely switch their positions. With all that in mind, I re-tested my unassigned, pasted swarm -- and got it to work by assigning the swarm to me only (the GM) and giving it sight. I could send it behind the character or move it back on top -- but then "to back" stopped working for everything else (other monsters, NPCs, etc.) since they were unassigned and unsighted. To send the swarm behind them, I had to remove "has sight" from either the swarm or the character -- and then turn it back on when I wanted the swarm to go on top of the character again. So, in summary, if two tokens are both assigned and sighted, you can move them front and back relative to each other . However, those settings also force the tokens to be "always on top." To change that, either a) the "blocking" token must also have both ownership and sight so you can use "to front" or b) the "to be blocked" token must lose sight or ownership. If it's a character, you can toggle off sight and watch it disappear behind another token that was moved "to front." I'm glad I figured it out, but it's frustrating there isn't a command or setting that always works . The workarounds are OK, but unless you make all your monsters, NPC and scenery tokens owned and sighted, you won't get consistent results with front/back. And even if you did, doing so ruins fog of war and dynamic lighting for those who use it. Is this really how roll20 is going to leave it, or is it being looked at?