Lewis, there are 4 choices of different settings for diagonal measurements of the ruler. The behavior of this can be changed by the GM under Page Settings. The measurement setting you would like is, from the sounds of it, the one called Euclidean . Wiki Docs, <a href="https://wiki.roll20.net/Ruler" rel="nofollow">https://wiki.roll20.net/Ruler</a> <a href="https://wiki.roll20.net/Page_Settings" rel="nofollow">https://wiki.roll20.net/Page_Settings</a> There are four options for measuring diagonals: 1. D&D 4E Compatible is the default setting. This measures a diagonal move as 1 unit. This simplifies the counting of squares at the expense of realism. 2. Pathfinder/3.5E Compatible measures a diagonal move as 1.5 units (rounding down). Thus, when 1 unit equals 5ft, diagonal moves alternate between 5ft and 10ft increments (i.e. 5ft, 15ft, 20ft, 30ft, etc.). This is slightly more complicated to count, but models reality more closely. 3. Euclidean measures diagonals using the Pythagorean Theorem. A diagonal move equals about 1.414 units using this method. This is also called the "real distance" or "as the crow flies". 4. Manhattan measures a diagonal distance as the sum of its horizontal and vertical distances. Effectively, a diagonal move equals 2 units using this method. This is also called "Taxicab geometry" or "rectilinear distance".