Abstract: A system for installing a drainage structure in the subsurface. The system has a casing, a drive device, and at least one fin. The casing has opposed first and second ends and defines a hollow region. The drive device is supported at the first end of the casing and configured to drive movement of the casing in a first direction. The at least one fin projects from the casing into the hollow region and is configured to buckle a corrugated metal culvert positioned at least partially within the casing when the casing is driven in the first direction. The drive device may be a pneumatic hammer or puller attached to a rod pulling machine.