Rail grinders and related methods of rail grinding in which custom grinding patterns are continually updated based upon an operational status of the rail grinder. The rail grinder includes a plurality of individual grinding modules that are individually arranged to generate the custom grinding patterns for individual rail segments. The custom grinding patterns allow the rail grinder to grind a desired rail profile for each rail segment in a minimum number of grinder passes and at a maximum operating speed for the rail grinder. Utilizing a variety of inputs including current rail conditions, desired rail profile, rail segment type, available grinding modules and grinding module style, a processing system either on-board or remotely located from the rail grinder can iteratively develop a custom grinding pattern that is temporally unique to each rail segment.