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[quote=Anonymous]OP here.  Just wanted to report back in case anyone ever finds this thread when searching with a similar question.

I persisted with the potty training pretty passively.  We kept him in underwear, with diapers for naps and overnight.  Occasionally, we would really pressure him to stay on the potty when we sensed he might be about to pee, so that he could experience success.  For the most part, though, I just let him keep having accidents.  (But it was manageable because he had learned to hold it so well that he was only having 2-3 accidents per day.)  I also encouraged him to sit on the potty a few times a day (and I gave him incentives to do so, like letting him watch Elmo or Thomas videos).

Anyway, last Thursday, the light switch flipped.  He peed in the potty on his own in the morning, and then again and again the rest of the day.  We've now had five straight days of no accidents.  He has peed on his toddler potty at home, the adult toilet, a toilet at the mall and a handful of other public places, and he peed outside on the grass once.  He's even had one poop success, though he's mostly still saving that for nap and nighttime diapers.

Anyway, we switched to underwear on 7/16, and he finally figured it out on 8/11.  I don't at all regret waiting it out.  He is VERY proud of his new mastery.  I know that potty training often comes in fits and starts, so I'm prepared for the inevitable regressions.  At least now I'm confident that he understands and can control the mechanics of it.

So I mostly wanted to update that it IS possible to potty train a boy at 2 years and 7 months (and isn't automatically "too late" or "too early").  And I wanted to express appreciation for the PP who pointed out that my toddler was having to unlearn everything he'd known for 2.5 years--that is, that he was supposed to pee in a diaper.  As a teacher, I'm more-than-familiar with concepts of "unlearning," so that framework was really helpful in this context.  My toddler just needed time to figure it out, and I had to be patient.

And, again, I'm not trying to be smug here.  We've still got a long way to go since he's still in naptime and nighttime diapers.  But I just wanted to provide some hope to any one else struggling with potty training.[/quote]

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