For me the fundamental thing here is the ability to see "inside" an object without being able to see "beyond" it - like the tree trunk example. One-sided DL lines would obviously be the easiest way to make this happen - you can see from the "outside" to the inside but not vice-versa. This isn't going to fix the elevation problem, however, since a token placed "inside" the boundaries of a vision-blocking obstacle (because they're actually on top of it) won't be able to to see anything outside at all - the opposite of what was intended. Attempting to deal with elevation effectively in what is fundamentally a 2D application is extremely challenging and I'm not sure there's really a good way of doing it. Even if you gave every object on the canvas a height property and calculated all the sight lines in 3D, it is liable to be immensely confusing in practice without a 3D visualisation. A top-down view relies on being able to "see" more than you should really be able to see precisely in order to compensate for not being able to see vertical surfaces - which is why the "see inside" use case comes about in the first place. The only real solution to this is to build a genuinely 3D tool, and quite apart from the practical infeasibility of Roll20 rebuilding their whole platform, it would introduce significant additional complexity for the GM in setting up the maps in the first place. At this point I think we need to remind ourselves that this is supposed to be a virtual Table Top , not a FPS computer game. The value of Dynamic Lighting (to me, at any rate) is to provide a more or less immersive experience during the exploration part of a game. It allows players to "discover" the map bit by bit, and feel, to some extent, the claustrophobia of a dark dungeon. But once you get into a tactical situation, I feel like it's better to remember the tabletop roots of the game we're playing - in some ways it's just easier to make everything visible at that point, and rely on the players and the GM to communicate about who can see what. If you really want to introduce new tokens by surprise at this stage, there's always the Bump script and the GM layer. I don't think that we should be asking the dynamic lighting system precisely to represent tactical LOS during combat. With that in mind, I think the elevation problems could better be handled by providing some more sophisticated tools for the GM to reveal/hide things. At the moment, one of the big limitations is that you can't easily introduce new parts to a scene with corresponding dynamic lighting paths. Being able to define sections of the map that group everything - map objects, DL paths, tokens - and which can then be hidden or revealed as a unit would give GMs tools to do progressive reveals manually for immersion and atmosphere without overly complicating the toolset or its implementation. A separate layering system that is orthogonal to the current one, or a more intelligent grouping tool would both be options here. But as far as this specific suggestion goes, the "see inside but not beyond" thing still very much has my +1.