Portable concrete barrier (PCB) systems are utilized in many situations, including placement adjacent to vertical drop-offs, work zones, and construction areas. Free-standing PCB systems are known to have relatively large deflections when impacted, which may be undesirable when dealing with limited space behind the barrier, such as on a bridge deck or with limited lane width in front of the barrier system. The risk of injury to workers in the work zone or construction area from displaced PCB systems is great. In order to allow PCB systems to be used in space-restricted locations, a variety of PCB stiffening options have been used, including beam stiffening and bolting or pinning the barriers to the pavement. This research evaluated the safety performance of the New Jersey Department of Transportation (NJDOT) PCB, Type 4 in various stiffening configurations according to the Test Level 3 (TL-3) criteria set forth in MASH 2016. All tested configurations successfully met all the requirements of MASH 2016 test designation no. 3–11 which was a 2,270-kg pickup truck impacting at a speed of 100 km/hr and 25 ∘. This research further reviewed and correlated stiffening techniques to dynamic deflection and working widths, as well as barrier segment damage. Implementation guidance is provided for the various PCB stiffening options to help protect the workers in work zone and construction areas.