The sun was starting to go low in the sky and the track was moving fully into shade as Bobby Labonte spun in turn 4 on lap 99, bringing out the second caution of the evening, just after Dale Earnhardt Jr had managed to crack the top five with a pass on AJ Allmendinger. Junior was looking curiously strong tonight, and his massive fan club was roaring its approval at every step of the way.
With track temperatures still at 120 degrees despite the setting sun, ice and water was the order of the day from the broiling drivers. Kasey Kahne got more overheated than anyone, with a pit lane speeding penalty sending him on a drive-thru before the restart on lap 103. After Hamlin, Kenseth and Edwards all needed adjustments in pit lane, it was David Ragan who won the race back to the track followed by David Reutimann and Juan Montoya with Hamlin and Kenseth dropping back to fourth and fifth.
Matt Kenseth was quickly back in the lead, while further back this stint was undoing all Dale's good work as he got loose and fell off the pace and out of the top ten, getting passed on all sides - he'd have to work his way back up all over again. Denny Hamlin was up into second place, but on lap 138 he was passed by Carl Edwards and he was soon on the radio to say that he feared the engine was failing on him. "It's dying", he mourned, but in fact it kept on ticking.
Kenseth dropped the lead for just a single lap during the next cycle of green flag pit stops. Kurt Busch was one of the few drivers to seem completely happy with how his car was running and just took tyres and fuel, but a dozen laps later he suddenly felt one of the wheels go loose and was forced into a second visit to pit road under green flag on lap 160 - a costly loss of time that put him a lap down.
Kurt's luck was somewhat in, however, as the next 22 laps saw a sequence of rapid fire cautions - for debris on lap 171; for Jamie McMurray blowing an engine on lap 182; and for Casey Mears and Landon Cassill making contact on lap 188. By the end of it, Kurt was back on the lead lap again and what had looked to be a horribly fruitless slog of an evening was looking rather better for the elder Busch sibling.
Things got back green flag racing for an extended period from lap 193, with Kenseth back in the lead ahead of Marcos Ambrose, Denny Hamlin, Carl Edwards and Juan Montoya; Ambrose got the better start and took the lead for half a dozen laps but Kenseth was soon back in charge again and starting to pull away.
Heat was still a chronic problem for almost everyone, with David Ragan even reporting that the ice he had taken at the previous pit stop was now turning to steam in the car and literally cooking him; just as well Kimi Raikkonen hadn't got it into his head to try this Sprint Cup race as well, after his highly vocal heat- and water-related trauma in the Nationwide on Friday night. As a new cycle of pit stops began with Kevin Harvick on lap 221, everyone was calling for more supplies of water and ice to be ready for them.
While Dale Earnhardt Jr. stayed out to lead a lap, everyone else sequenced through pit road; Regan Smith came in to pit lane only to have a missing lug nut on exit and be recalled to pit road. Tony Stewart sought an off-sync pit strategy and stayed out accompanied by Kurt Busch; Stewart had finally come into the pits ceding the lead to Busch when the sixth caution of the night came out for Mike Bliss stalling on track near to pit road. That gave Busch the chance to pit under caution - most satisfactory for the #22, all things considered.
Marcos Ambrose led the restart on lap 237 just after sundown, ahead of Kyle Busch, Denny Hamlin, David Ragan and Paul Menard: but Menard got high, lost grip on the marbles and hit the wall in turn 2 to then spin down the track without collecting anyone bringing out the seventh caution three laps later, with Martin Truex Jr. also sustaining rear end damage when Brian Vickers ran into the back of him in the aftermath.
At the next green flag, the demon restarter Kyle Busch nailed it and easily took the lead from Ambrose, and led through to his next green flag pit stop on lap 278 - but the pit sequence was interrupted a few laps later by another caution on lap 282 for debris in turn 3. Once again the race sank into a repeat cycle of rapid yellows, with a ninth caution on lap 289 when David Starr hit the wall, and a tenth when Landon Cassill slid through the grass on lap 295 after getting tapped into a spin by Regan Smith. Cassill even reprised Carl Edwards' feat of last week of caving in the front of the car in a dip in the undulating surface as he went.