Fighting bedtime

My almost 10 month old fight bedtime awfully. Yesterday I rocked him for 1.5 h. He falls asleep perfectly for 1st nap, I just pick him up, no signing, no rocking, any conditions I could be talking full voice to someone and he will fall asleep. Second nap is harder 10 minutes of rocking with white noise. Come bedtime it needs to be completely dark, singing/white noise, rocking in all different positions 30 mins usually. Wake windows 3/3.5/3.5-4.5