It might be possible in some cases to simulate height differences with the "One-Way Dynamic Lighting" API script(available for Pro subscribers). Unfortunately it's doesn't seem to be a practical solution for your war-gaming, as it the trick the API uses results in all players sharing vision for the one-way DL segments. On a positive note I tried to use the script, but didn't figure out how to make it work. I don't really GM on Roll20, so not too familiar with DL or API scripts, but someone who knows this stuff better might figure out something useful from this. The script's author had an interesting comment about the future of One-Way Dynamic Lighting(emphasis mine): There are some paradigms I've considered when implementing this script that would allow each character to have their own perspective of the dynamic lighting . Unfortunately, this would only be possible if it were implemented in Roll20's dynamic lighting system itself using some WebGL magic involving stencil buffers and lighting polygon unions. A while ago, I presented an algorithm for implementing one-way dynamic lighting in the dynamic lighting system . If it's compatible with their current system, maybe the Roll20 developers can make use of it. For the time being though, I hope that this humble script will suffice for everyone's one-way dynamic lighting needs. Beyond just improving performance and all the other things, the fact that Roll20 is working on recreating DL and FoW in WebGL will mean more features will be possible to implement, and give more options for API as well.