My boyfriend is on probation for possession of marijuana and got pulled over yesterday for driving on a suspended license. Are we looking at jail time here and how long? Should he tell his P.O?

Yes he needs to tell his PO
At maxium he will have to serve out his time on the prior and get sentenced for the new charge.

At minimum it would be something like do his Probation time and have a fine for driving with suspended license.

So is he pretty much going to have to serve out the rest of his probation time in jail? That's the minimum?

I think the maxium would be serve out the probation time in jail along with whatever they do about his new charge.

Do you think it could be based on whether his officer likes him or not. Because I read they could give him a second chance if he's already done everything he needs to do .

If all he got was a driving with suspended license. I think how easy they go on him can be determined by how cooperative he is and has been and reporting it to his probation officer.

I'm hoping maybe if we get him a lawyer specializing in probation violations that may also drop it down a few notches.

If this new charge resulted in his going directly to jail and having to be bonded out, then it will really matter as he will have violated his probation. If he does not tell his PO right away, the PO is going to find out anyway. I don't think it's going to be something he can just brush under the rug either if he is convicted of driving with a suspended license. This is not a crime that you just get a ticket for. He needs to retain an attorney to help him straighten out his mess. He just might end up doing his probation time in jail. You didn't mention if this was a misdemeanor or felony probation. It does make a difference in what happens next.

It's a misdemeanor probation

Then if it was a misdemeanor, things should not go so bad for him.

When you say things shouldn't go so bad, what do you think we're talking here sentence wise. What do you think a lawyer would be able to do for him probationwise. Were looking at lawyers that specialize in probation violations

A lawyer 'looks' good in court to the Judge they tend to go harder on you when you decide to not get a lawyer.
Him telling the PO also makes it better because when you don't it looks like you are being uncooperative and trying to conceal things.