The requirement for the calculation of microwave link path loss has received considerable attention over time and a number of path loss prediction algorithms have been created. Many of these however are based on theoretical calculations using idealized obstacles so that the actual measured path loss will deviate significantly from calculated values. Through the use of modern computing techniques, algorithms can benefit from the use of experimental data to better approximate loss due to actual terrain features. This paper outlines results of measurements taken involving diffraction loss over various obstacles.