The agent will read your policy literally

Late checkout cost extra. It said so on the website and on the card in every room, and when I was a manager at a hotel, I waived it all the time.

I'd waive it for a guest whose flight got pushed, or for a couple on their third stay that year. And for anyone who'd had a rough night because the room next door was loud, which was our fault, not theirs. None of that was written down as a rule. Whoever was at the desk read the situation and made the call, and it was usually the right call, because you could hear it in how the guest asked.

The fee had a job, too. Housekeeping needed the room, the next guest was waiting on it, and the desk needed something firm to point to when someone just wanted a free afternoon. So the real policy lived in two places. The card said noon, and the desk knew when noon wasn't the point.

That works as long as a person is asking a person. I don't think it survives a customer sending an AI agent instead.

An agent is likely to read the written policy the way it was written. If your return window says a month, it can file on the last day and expect the refund, without the apologetic tone a person uses when they know they're pushing it. It's unlikely to ask for the exception your team would have happily made, because nothing it can read says the exception exists. So the guest with the delayed flight could end up paying the fee, while whoever knows exactly where the line is gets everything the words allow.

I don't know how fast this shows up for any particular business. But the gap was there when I was managing. Written policy and actual policy had drifted apart long before any agent, and the difference sat in the heads of the people who handled the exceptions.

I think that difference is part of your policy now, and it should be written down like it is. Ask your team to list the exceptions they actually make in a normal week, then mark which ones the written policy covers. An agent is unlikely to ask for any of the ones it doesn't.