Yes, ICON systems are compatible with Chevy Trail Boss trim packages. The Trial Boss comes from factory with a  2” higher ride height. The max lift height over stock will have to be adjusted for these models. For example, the ICON system is rated to be capable of achieving 3.5” of lift overstock. Where a trail boss will only achieve 1.5” additional inches of lift overstock because the vehicle starts 2” closer to its max from the factory. Please call ICON tech-support for more details (951) 689-ICON.