While working for a private IFT company, I would sometimes go to various incarceration facilities around Maryland, usually to return a prisoner to the jail or prison, or sometimes to take one with chronic problems to a medical appointment outside the facility.
One time, I was sent to Baltimore's prisoner infirmary to return a prisoner to another building, which was practically across the street. The policy for the jail system is that a pair of guards from the destination facility must accompany the prisoner. So we get to where the prisoner is, then have to wait about an hour for the guards from the destination to show up. Now, this prisoner was there for a broken leg, so he had a big thick cast on his left leg. The guards begin to cuff and chain him, as they are supposed to do. Now, the handcuffs are supposed to get locked to a big leather belt that goes around the waist, so the prisoner cannot raise his arms. But this guard had a hard time doing this, and in fact the patient (the prisoner) wound up helping her out. Then the guard went to put the leg irons on, but realized she wouldn't be able to shackle the left leg due to the large cast. So she had the bright idea of cuffing the right leg to the stretcher frame instead.
This probably would have been a good idea under the circumstances, except what she actually cuffed him to was the IV pole that was collapsed and snapped down. So really, his legs weren't secured at all. I decided not to say anything about it, figuring he wasn't going to get vary far, what the cast on and his arms/hands shackled the way they were. So I said nothing. Anyway, we transported (across the street) without incident, and bring the patient in to the intake area for him to be processed back in. We are directed that the patient can go ahead and get off the stretcher and sit on one of the benches, and we can leave. The guard starts unshackling him, but seems to be having trouble uncuffing him from the stretcher. I don't think she had a bad angle to get the key in, or something, whatever.
I saw her having trouble, and I was extremely tempted to just lift the IV pole up and slide the cuff off—I really, really wanted to. But something inside me said no, don't embarrass her like that, don't make her look any more incompetent than she's already made herself look, not in front of a prisoner. So I just left her to figure it out for herself.