Depending on the amount allegedly stolen and the jurisdiction where the event occurred, shoplifting can be met with a mere citation (infraction), or charged as a misdemeanor or even a felony, with possible jail sentences of 6 months to 3 years. It will be up to the D.A. to determine how the crime will be charged. I suggest that you hire an experienced criminal defense attorney to represent you and get you the best deal possible.
Instead of worrying about the jail time, you need to focus your attention on how you can avoid being convicted. Time to shop for a lawyer, because you face a potential felony this time.
You could go to jail for up to a year. Second offense appears that you have not learned from your last run in. I would also expect that you have stolen far more than 2 times, but have only been caught twice. Based upon what you told me, if were sitting as judge and you were convicted, I would order jail time.
That all depends on how the judge in your area handles those types of cases. However, if it is your second offense it is more likely you would do jail then if it were only a first offense. It also probably means you're no longer eligible for diversion programs. You could be placed on probation as well.
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