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Hey there, do you have a save to attach that had this issue? I used the one you attached and you can see what happened below.
I did get them placed, there was a small issue in that the first prisoner I told to get a tracking belt, it said there were no belts, when there was a box in the infirmary. However, manually telling the prisoner to be escorted to infirmary cleared this up and they were given a belt. The second prisoner was given one with no issue.