What is the regulation for punishing a soldier multiple times for the same offense?

The regulation is that you do not administer punishment, the commander does. Push-ups and writing essays are not a punishment, they are corrective training. A leader may direct as much corrective training as they see necessary to correct a deficiency. If it takes push-ups, writing an essay, giving a class, and digging a foxhole to get through to that Soldier, that leader has the authority to do so.

NJP is punishment. Court martial, confinement, loss of rank, forfeiture of pay, extra duty, manual labor (in prison), all directed by the Commander, are examples of punishment.

SGT (Join to see) If the Soldier continues to commit the same offense, his leader has not been assigning effective corrections!

Well, in a sense, yes. Especially if he is repeating the behavior that gets him smoked/counselled, etc..

But, if he made the mistake only once and the corrective action was completed and the behavior changed...then logic dictates that he shouldn't be smoked/counselled for it again. But, to get the best and most correct answer possible, I would contact JAG for this one.