Usually one of the conditions of probation is that the probationer be either gainfully employed or be enrolled as a student. I believe the answer to your question is yes.
In Florida, they certainly could- one of the probation conditions is that you be gainfully employed, or actively seeking employment, or become a full time student.
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Why would you not want to get a job? Gainful employment is often a term of probation. Read you probation order carefully. If you want to impress your PO with you strong desire not to work, watch out down the road for more violations.
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Yes, especially if you are in some type of program like Drug Court. Getting a job or at least attempting to get a job is a specific term of a Drug Court contract. It is not so much the Probation Officer personally, but rather the PO attempting to enforce the terms of a contract or a Judgement and Sentence.