Studies on eco-driving have mostly taken an energy-centric view and considered driving performance, while less attention has been paid on emissions behavior. This work extends in an experimentally verified way our understanding of the trade-offs among fuel economy, driving aggressiveness, and, especially, emissions in connected automated diesel-powered vehicles. Experiments are performed with a 6.7-L Ford Powerstroke diesel engine, a urea-SCR based NOx aftertreatment system, and a full model for a Ford F250 medium-duty truck in the loop to provide realistic assessment of fuel consumption, tailpipe emissions, and driving style performances. An energy and emissions conscious speed planner is leveraged to follow the traffic. This planner offers flexibility in prioritizing energy or emissions while satisfying user-defined headway constraints, and thus allows exploration of different calibrations in a unified way. Results show how various calibrations of the flexible leader following policy yield 8%–14% decrease in total fuel consumption and 64%–70% decrease in tailpipe emissions compared with a strictly constrained following policy.