I find it hard to believe that a judge would have decreed that a PO could not go to the employer work place. Your friend broke the law. He can make requests and while judges can be accomodating I can't imagine one straight up telling a PO not to utilize all the tools at their disposal, to make sure that your friend (the person convicted of a crime) was following the rules.

As for the timing, well, if your friend is right about to finish probation, this is literally when the majority of POs I've dealt with will check to make sure you're not breaking the rules. Lot of people get stupid and complacent when they see the finish line. I've seen a ton of probationers get caught with less than a month left.