I will say that no, there is never a time to punish during TT as it would be counter-productive. You don't want him to get scared of going to the toilet
My two boys were TTed at 4 and 3 and a 1/2. They weren't interested any earlier so I would say at 3 and a 1/2 with only random accidents is good (for me anyway).
Have you tried getting him to help clean up?
Oh, and TT wasn't my hardest parenting challenge. I was lucky and it went very smoothly. My hardest has been brushing teeth and washing hair. It is still a nightmare.
I agree with chocaholic, I don't think kids should ever be punished for toileting accidents, even if they're not so accidental.
I would be getting him to clean his own messes up though (with in his capabilities and with supervision). Give him as little attention as you can in regards to an accident, as then there is little pay-off for him (eg, if he wets/soils himself and you clean him, you're having a rather intimate and long interaction). So get him to wipe up his own puddles, wipe his own bottom, get his clothes and dress himself.
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