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First off, I've got an 05 with the TowCommand. The trailer is hydraulic/electric which the TowCommand does not support (come to find out). Carslisle makes an actuator that is compatible and has since been installed on the trailer.
Upon testing this is what happens:
Trailer brakes do not activate via the pedal, but the trailer marker lamps illuminate.
Trailer brakes will activate with manual dash control and trailer marker lamps illuminate.
Dash Towcommand display appears normal showing green trailer and gain (set at 8.0.)