This paper investigates tool path planning for 5-axis flank milling of ruled surfaces in consideration of CNC linear interpolation. Simulation analyses for machining error show insights into the tool motion that generates a precision machined surface. Contradicting to previous thoughts, the resultant tool path does not necessarily produce minimal machining error when the cutter contacts the rulings of a developable surface. This effect becomes more significant as the distance between two cutter locations is increased. An optimizing approach that adjusts the tool position locally may not produce minimal error as far as the entire surface is concerned. The optimal tool path computed by a global search scheme based on dynamic programming supports this argument. A flank milling experiment and CMM measurement further validate the findings of this work.