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This paper investigates the insensitivity of propositional surprise ‘how’ in English to the so-called Inner Island Constraint. We first characterize this type of ‘how’ as distinct from other familiar types of manner, method, and degree ‘how’. It is supposed to prosodically bear nuclear accent, syntactically trigger Subject-Auxiliary Inversion, and semantico-pragmatically reconcile the post-‘how’ proposition with the rest of the speaker’s beliefs. On its syntactic and interpretational parallelism, we propose that this type of ‘how’ is generated in [Spec,CP] like ‘how come’ reanalyzed in the Comp position and identically to ‘why’ generated in [Spec,CP]. We also examine what Pesetsky (1987) dubbs as aggressively-non-D-linked elements like ‘the hell’, which is accompanied by propositional surprise ‘how’. Since the use of ‘the hell’ presupposes a possible lack of a definite answer to the wh-question, and if the answer exists, it’s not known to the speaker, ‘the hell’ is most appropriate to propositional surprise ‘how’ questions. By exploring the formal properties of this construction, this paper seeks to make significant contributions to our understanding of the intricate interplay between syntax, semantics, and pragmatics in the English language.