Will I bet jail time fore a second offense driving after revocation?

OAR is a class A misdemeanor punishable by up to 9 months jail and/or a $10K fine. So, yes, you are facing jail time. Whether you will actually be sentenced to jail time depends on the jurisdiction, the facts of the case, the prosecutor, the judge, etc. There are certain judges in Waukesha County who are now sentencing OARs to jail for first offenses. So, the fact this is your second offense within a year makes it more likely you will receive jail time. The fact you have had 5 DUIs makes it REALLY likely you will receive jail time. Consult with local, experienced criminal defense attorneys immediately. If you cannot afford an attorney contact the local public defender's office. If you do not qualify for public defender assistance, then ask the court to appoint a low cost attorney to your case. Good luck!

While I agree with the previous answer to some extent Where I practice OAR's that are firsts rarely get jail. But it does depend on the case. Also, I believe that the penalty range is only up to a $2500 fine but up to one year in jail under sec 343.44(2) of the statutes. So you could be looking at jail although it would be pursuant to the local guidelines for OAR that your county has implemented which are most likely far less than that maximum on a first. Talk to a local qualified attorney. Good luck.