Testing station analogs, binaries, and controls of a RTU at a single substation can be time consuming and error prone. Multiply these challenges by 600 substations and suddenly these challenges can seem insurmountable. This is where the power of software automation can deliver efficiencies and eliminate human errors. This paper summarizes the approach used and lessons learned when automating the point-to-point testing of the legacy D20 RTU. Automation included creation of test plans by sanitizing data from multiple sources, live testing automation with a text-based user interface for the tester, and the automatic recording of the test results.