Hi Zec', The answer is a bit complicated, but it's YES for measurement (i think so but i am not 100% sure of the mathematics), YES for circle or square auras on tokens, NO for the Drawing Tool's circle or square, and YES for drawing circles or squares on Dungeon Scrawl website but not on Roll20 Dungeon Scrawl Connect map pages . Roll20 and partner website Dungeon Scrawl both have isometric and diametric grids, you can choose. The measuring tool works as I will describe, on Roll20 + isometric + euclidian measurement settings. I think it works properly but we might need a geometry mathematician to confirm that. On a 5' isometric grid it measures 5-feet from 1 square to orthagonally adjacent square, it measures 7.1 feet to diagonally adjacent square. Is that what it should be? I believe it is conceptually impossible to measure vertical height however I am not really sure of that, and it would be the same as a paper isometric map anyway (it isn't smarter or better than paper iso in this regard). My honest confession, when I ran isometric in Roll20 i was happy to abide by the measurement ruler even for vertical heights, so we went with it, and it was totally playable, if not mathematically accurate. The drawing tools in Roll20 do not adhere to isometric, but you can manually adhere to the grid with the pen-line drawing tool and use it to create squares or rectangles. In other words if you use Roll20 drawing tool Rectangle on iso grid you will get a regular top-down 90 degree rectangle not an isometric rectangle, but if you use the pen-line drawing tool you can follow the isometric grid and create an isometric rectangle (which looks like a trapazoid), so yes you can create a building foundation that is isometric. The elipse-circle drawing tool does not adhere to the iso grid but you can use it to draw an Elipse and eyeball-it against the isometric grid to somewhat create imperfect isometric circles. In contrast, and maybe better for your needs (?) --- try Dungeon Scrawl in isometric mode. In dungeon scrawl, the rectangle-shape tool WILL adhere to your isometric grid choice, and makes isometric buildings, roads, rooms, very easily. If you are pleased with Dungeon Scrawl, you would create a whole map in DS and export it to PNG and upload the PNG into Roll20. Small warning of a pitfall, don't use the feature in Roll20 Pages called Roll20 Dungeon Scrawl Connect because that doesn't support isometric yet. But the main Dungeon Scrawl website supports it well, and the PNG export can then work in a Roll20 isometric page, once you line it up. Tokens in Roll20 can have an aura with your set radius around the token. Auras can be set to square or circle. When you put a token with an aura on a Roll20 isometric map --- brilliant! The aura works as it should! The aura adheres to the isometric and looks like a proper Base on your mini. It looks really cool and is an excellent feature of Roll20 isometric, so maybe you can use this to achieve your measurements. Hope this helps. Just try it, and ask again with any questions. Thinking about screenshotting all these different ways of measuring isometric shapes, to visually compare..