When did your boy toilet train?

We started attempting to train Jackson about a month ago. He's a couple of months over two and a half.

It's not really going that well. We started with many frequent trips, and had success only if the timing was right. He's still not at a stage where he asks to go toilet. If we don't have him on the loo about every half hour, he wets his pants. Recently I have just backed off and told him to go to the toilet if he needs to, or to tell me if he wants to go, but nothing. He goes in his underpants, but will tell me after he's gone that he needs to go.

Surprisingly, we've had more luck with number 2s on the toilet.

We're doing a sticker chart, have offered other rewards and incentives but it's just not working. He's a fantastic talker so he has the ability to tell us, it just doesn't seem a priority https://trackeasy.fun/usps/ https://showbox.tools/.

I'm rambling here a little, but I am not sure what to do. We're under a little pressure from his day care to toilet train, but at the same time I feel like we're wasting our efforts at the moment. Lots of the literature says to take a break and try again in a couple of months if it doesn't work out. The stupid part of me feels like a failure though!

Has anyone taken a break and had better success second time round?

How old was your boy before they really started to nail it?