When a probation violation is extremely severe which it appears in the case you've detailed in your question, a probation revocation hearing could be scheduled. There is no set rule as to what happens immediately after a probation violation is reported. If they are found guilty of probation violation, sentencing will occur shortly after the probation hearing, at which time the court could extend the probation length, impose additional probation terms, order you serve time in jail, or revoke your probation altogether and require you to serve out any remaining time of your original sentence in prison. Factors a judge may consider in determining your sentence may include the nature and manner of the offense and whether the offender was a "first-time" or "repeat" offender, among other considerations. Our opinion on your boyfriend's situation is that there will be a revocation and there will be a lengthy prison sentence to follow based on what appears to be a disregard for the probation process. The new charges do not look good after he was given some leniency being offered probation.