With increasing penetrations of inverter-based, renewable energy resources on electrical grids around the world, new distributed energy resource (DER) interconnection and interoperability requirements have been introduced to address emerging power system operator needs. The inverter-based power conversion systems are capable of communicating with grid operators, providing voltage and frequency support, and supporting the grid during faults. However, DER vendors are under pressure to quickly and reliably update the interoperability and electrical capabilities of their equipment for different jurisdictions with the rapidly changing landscape of disparate codes and standards. The necessary power hardware required for testing Advanced Microelectronics and Radiation Effects, Sandia National Laboratories, Albuquerque, NM, USA power systems under the wide variety of operational conditions may be untenable for many organizations. Therefore, we introduce an approach for the concurrent development of controls and application software through a controller hardware-in-the-loop (CHIL) testbed integrated with an automated testing platform that allows for the cost-effective, flexible evaluation of advanced grid support functions without the need for large and expensive power hardware. We show this CHIL capability through the demonstration and automation of interconnection tests with a 34.5 kW Austrian Institute of Technology (AIT) smart grid converter (SGC) connected to a Typhoon HIL system. We have demonstrated the CHIL system with regards to connect/disconnect, active power curtailment, fixed power factor, reactive power control, volt-var, and frequency-watt advanced grid functionality tests. For all tests, the automated CHIL testing protocols for advanced functions were sufficient to demonstrate and evaluate the grid support behavior of the equipment under test.