Let $\alpha$ denote an ordinal. Then clearly, the powerset $\mathcal{P}(\alpha)$ has well-founded subchains that are maximal with respect to this condition (of being well-founded subchains), since $\alpha$ is itself such a subchain. Nonetheless, $\alpha$ is not maximal with respect to the condition of being well-founded, since adjoining any element of $\mathcal{P}(\alpha) \setminus \alpha$ to $\alpha$ yields a larger subset that is still well-founded.
Assume $\alpha$ is an infinite ordinal; without loss of generality, assume it is the initial ordinal of some cardinal.
Question. Does $\mathcal{P}(\alpha)$ have well-founded subsets that are maximal with respect to this property (of being well-founded)?
I feel that this is impossible. Suppose for a contradiction that $\mathcal{X}$ is a maximal well-founded subset of $\mathcal{P}(\alpha)$. Then $\mathcal{X}$ must contain every finite subset of $\alpha$. Hence $\mathcal{X}$ must contain an infinite element, call it $A$. Assume for simplicity that $\alpha$ is countable, and hence that $A$ is countable. Let $f : \omega \rightarrow A$ denote a bijection.
Okay, where can we go from here?