I hate to sound like a broken record, but he's UT first thing in the morning and that's why you can't extend. He was up less than 2hr and took a 47min nap, that was unextendable (classic UT). Then, he was up for over 2hr and ended up taking a 2.5hr nap in total. Sure, you needed to help him get to sleep and resettle him, that was a long time to be up after a short nap and he was OT, but after you resettled he slept 2hr, so he wasn't so OT that he couldn't keep sleeping. This tells me that he resettles and sleeps when he's tired enough to do so.
Start pushing the A times. You may need to help him to sleep a bit and resettle him when he wakes for a few days, but his body will adjust to staying awake later.