But if the agent can't be subject to Dutch books
You avoid falling into Dutch book loops where you iterately pay to go around in a circle at each step, but you still fall into single-step Dutch books. Unnamed gave a good example.
Those aren't technically Dutch Books. And there's no reason a forward-looking unlosing agent couldn't break circles at the beginning rather than at the end.
Some have expressed skepticism that "unlosing agents" can actually exist. So to provide an existence proof, here is a model of an unlosing agent. It's not a model you'd want to use constructively to build one, but it's sufficient for the existence result.
Let D be the set of all decisions the agent has made in the past, let U be the set of all utility functions that are compatible with those decisions, and let P be a "better than" relationship on the set of outcomes (possibly intransitive, dependent, incomplete, etc...).
By "utility functions that are compatible those decisions" I mean that an expected utility maximising agent with any u in U would reach the same decisions D as the agent actually did. Notice that U starts off infinitely large when D is empty; when the agent faces a new decision d, here is a decision criteria that leaves U non-empty:
That's the theory. In practice, we would want to restrict the utilities initially allowed into U to avoid really stupid utilities ("I like losing money to people called Rob at 15:46.34 every alternate Wednesday if the stock market is up; otherwise I don't.") When constructing the initial P and U, it could be a good start to be just looking at categories that humans natuarally express preferences between. But those are implementation details. And again, using this kind of explicit design violates the spirit of unlosing agents (unless the set U is defined in ways that are different from simply listing all u in U).
The proof that this agent is unlosing is that a) U will never be empty, and b) for any u in U, the agent will have behaved indistinguishably from a u-maximiser.