Due to their large size, mass, and high center-of-gravity, heavy vehicles, especially long combination vehicles (LCVs) require a substantial amount of space to negotiate turns, long distances to brake from highway speeds to a stop and are susceptible to rollover. Combination vehicles on the U.S. roads are commonly in 53-ft single trailer or 28-ft double trailer configurations. With the continual rise of e-commerce, package carriers are pursuing 33-ft double trailers to increase each vehicle's cargo volume. Before introducing these trailers into a fleet, there is a need to understand (1) if 33-ft doubles can negotiate existing routes traveled by 28-ft double and 53-ft single configurations, (2) if 33-ft doubles can benefit from existing stability control systems, and (3) how trailer brake types perform on 33-ft doubles. Three separate studies are conducted to address these topics. The first study compares off-tracking for the three mentioned trailer configurations through low-speed, real-world maneuvers via physical full-scale tests and simulation. Off-tracking is a metric illustrative of maneuverability and is defined as the relative distance in paths of the rearmost axle to the lead steer axle. New mathematical models are introduced and used to simulate vehicle motion through low-speed maneuvers. The simulation and field tests determine that, for all tested maneuvers, the order from smallest to largest off-tracking is 28-ft double, 33-ft double, and 53-ft single configurations, with the 33-ft doubles having slightly larger off-tracking than 28-ft doubles. This suggests that 33-ft doubles can travel through routes typically traveled by a 53-ft single but need slightly more space on the road than a 28-ft double. The second study tests 33-ft double trailers with and without stability control systems. Tests, conducted at a test track, are designed to replicate real-world maneuvers that induce trailer rollover. It is found that the 33-ft double trailers are clearly less likely to rollover with the tested stability enhancement systems than without. The tests also illustrate that the different tested control systems' effectiveness in reducing rollover propensity is maneuver dependent. The third study tests the braking distance, brake influence on the stability control systems, and rollover dynamics while braking-in-turn for two different types of brakes, drum brakes and disc brakes. Small but evident differences in the performance of the two brake types suggest disc brakes could provide shorter stopping distance and time at highway speeds, compared with drum brakes. The studies detailed in this dissertation provide valuable information on 33-ft doubles dynamics and provide guidance for their safe introduction on the U.S. roadways.