Disclosed herein are techniques for preparation of a bone structure wherein a robotically controlled cutting bur is utilized for both milling the entry point at the outer cortical region and cannulation of the cancellous bone region for receipt of an implant. A robotic manipulator supports and moves the cutting bur and one or more controllers analyze measurements from sensors and, in response, control the robotic manipulator and/or the cutting bur for purposes such as landmark detection to determine entry point, avoiding tool skiving at entry point, and avoidance of cortical wall breach during cannulation. Also described are techniques for managing feed rate, rotational cutting speed, or mode of operation depending on operational conditions surrounding various stages of cannulation. A control interface is also provided to enable the user to manage or adjust cutting bur operation and feed rate.