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chew--- You are correct. I just assumed the security officer was a Dart employee. My mistake.

The rust issue is not my concern. It is the fact that an earpiece or headphone is distracting the guard. I would initiate a company policy against such activity. Maybe an undercover type job evaluation is in order.
I would report this to DART.

Just from what you have told us ,she is getting a FREE RIDE in more ways than one.
I would express my concern to management and have them follow up on this.