When I was young, they used to send crews like that out without a guard. They’d do random drive by checks. Not there for a check, or not get back to the jail for supper, and it was a 5 year prison felony for escape.
Around where I live they use a lot of trustees. After the parades or festivals you will see these guys with a shirt on from the local jail and on the back of the the shirt it is written TRUSTEE. These guys work hard, will not talk to you or even make eye contact. I’m sure they are told not too.
In Mississippi at Parchman farm trustees if full leg stripe could carry a shotgun or 30-30 on work detail
The old days
And lived in trustee village with street food and women
Not a bad gig for the joint
My cousin spent most his adult life there