The next green flag lasted only four laps before the seventh caution on lap 229, resulting from a collision between Brian Vickers and David Ragan: Ragan got loose off the turn, and spun across the front of Vickers; the nose of the #6 embedded itself into the front left side of Vickers' car and then, as Vickers carried on past, literally peeled the skin off the side of the #83 like a can opener, leaving Vickers with major bodywork ripped off and flapping around, and impact foam all over the track from inside the bodywork.
The caution gave Martin Truex Jr. the lucky dog free pass, which meant that Kyle Busch was still a lap off the leaders. "What position am I now, please?" he radioed in rather bleakly, to which crew chief Dave Rogers responded succinctly: "21st".
Carl Edwards led the field to the green flag on lap 235 but quickly dropped two positions to Kevin Harvick and Kasey Kahne, before the race was immediately back under caution for Joey Logano spinning after contact with Marcos Ambrose. It was ironically good news for Logano's team mate, Kyle Busch, who finally got the lucky dog this time and was back on the lead lap again at last after that unfortunate loose tyre, and with plenty of time yet to make it back to the front.
Currently in the lead for the restart on lap 243 was Kevin Harvick, followed by Kasey Kahne, Carl Edwards, Jeff Gordon and Tony Stewart, but Busch served early notice of his intent to get back among them by some eye-catching aggressive driving, sweeping down to the inner apron to gain multiple spots without a second thought. He was back into top 15 by lap 263, only a few places back from Regan Smith who by now was lurking on the outskirts of the top ten.
Tony Stewart had just pitted under green for tyres and fuel on lap 278 when the ninth caution of the evening came out after Mark Martin smacked the wall, leaving the #5 sending up smoke signals. Stewart was fortunate to get the wave-around as the leaders came in for their stops under what should have been a less stressful yellow, but in fact there were multiple incidents on pit road including Paul Menard nearly running over the member of his pit crew who had been attempting to clean up the grille, and Jeff Gordon taking off with his gas man who was still pumping fuel into the back of the #24.
At the green flag on lap 284, Kasey Kahne has displaced Kevin Harvick during the pit stops and they were followed by Carl Edwards, Jeff Gordon and Dale Earnhardt Jr., who was the biggest mover in the race at this point having started from 30th on the grid. Further back, Jimmie Johnson was also back on the lead lap having received this caution's lucky dog - the latest of several big names needing that same get out of jail free card here tonight at Darlington.
A length green flag period followed, with Kahne maintaining the lead through to and after the green flag pit stops which started around lap 320. However, Carl Edwards was feeling very confident and reported to the team that he felt they had the car to beat tonight - all they had to do was get the #99 to the front. Other drivers were less happy with the state of affairs, with Johnson and McMurray both reporting worrying wheel vibrations before they came in for their respective pit stops. And worst of all, Earnhardt Jr. undid all that earlier good work with a spin coming into pit lane that saw him hit the commitment line cone, incurring a drive-thru penalty that ejected him from the lead lap.
With potentially the final pit stops out of the way, the drivers got down to the serious battle of the race endgame. Edwards asserted himself and followed through on his earlier boast, taking the lead from Kahne who wasn't wildly happy with the current state of his car: "I'm too tight," he radioed to his pit crew. "Tighter than the last time for sure"
Denny Hamlin had also emerged as a potent threat to the leaders, and it took a determined effort by Kevin Harvick to pass him on lap 335 which saw Harvick come close to spinning the #11 although no actual contact was made. Both cars survived the scare, with Hamlin now having to fend off the attentions of Regan Smith for fifth place, as Smith targeted a career-best finish (the previous best being seventh at this year's Daytona 500.)
The race was just ten laps away from its scheduled end when the tenth yellow of the evening came out, for Jeff Burton's car blowing up. He'd radioed earlier that his water and oil readings were all showing red lights, and now he knew that they hadn't been bluffing. The late caution now gave the crews the chance to bring their drivers in for fresh rubber - just two new tyres could make a race-winning difference at this point - and most of them did, although Jimmie Johnson would come to rue the decision after a fumbled lugnut saw him recalled for a second pass through to cap what had been a trying evening. A few cars gambled on staying out without fresh rubber: Regan Smith, Brad Keselowski and Tony Stewart took up the top spots. But it would take something big - ideally, another caution and a green-and-chequered finish - to make this Hail Mary pay off.