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Maybe move bedtime an hour earlier until you aren't working with such a sleep debt?

@Applesandbananas: Hmmm. How verbal is LO? When in the bedtime routine does the crying start?

Is he angry or just overtired? Is he trying to assert himself or his will with it?

We went through a phase a few months ago (right at 2.5) where bedtime became an utter (forgive the language) shit show. She would literally trash her room in protest, escalating if we tried to ignore her. She would throw all of her toys and books on the floor, all the while yelling, "I making a mess, Mama" at the top of her lungs and hysterically crying. At one point, she picked up her nightstand and hurled it across the room taking a chunk out of her footboard. Suffice it to say, it was horrific. We tried moving bedtime forward and back, but honestly, I think at the end of the day it was a battle of wills, and we were determined not to lose. We took out everything that wasn't bolted down for about a week, and then just sat outside the door making sure she was okay and telling her firmly that we loved her but it was bedtime. And eventually, she got the message and the phase passed. In sum, I've got nothing, but boy do I empathize and hope it gets back to normal quickly!

@Applesandbananas: Totally hear you. Mine was a terrible sleeper as a baby, but we'd had a simple and consistent routine that worked for a year when it all went to crap. I think all in, it lasted a couple of weeks, but then we settled back into our old routine and all has been generally well. I felt desperate at the time though and worried it was the new normal. We have since moved onto the creative excuse stage with requests for more water and more songs and more hugs and fake bathroom emergencies, ha, but she's at least calm when denied!

It's definitely a phase. Almost everyone in my mom group went through this around 2.5-3 years. Bedtime was taking us 1-2 hours and she wasn't asleep till 10-10:30. We moved bedtime up, moved bedtime later, no naps, naps, threats, bribes. You name it. It's a crappy phase.

We went through this too at exactly 2.5yrs, it was THE WORST. So much worse than any sleep issues we encountered when DS was a baby.

I don't have much advice as I didn't handle this phase very well at all It helped a little for us to set firmer boundaries/expectations and to react to his escalations by responding as calmly and quietly as my patience would allow. This lasted about 6 weeks for us and then things magically got better. Hoping your kiddo gets through this quicker than we did!