This empirical investigation shows that in certain contexts, surprise with an embedded whether-interrogative (polar or 'alternative') is in fact acceptable, contrary to a widely accepted judgment reported by Karttunen (1977). The context sensitivity of the judgments suggests that the use of surprise whether-sentences is subject to pragmatic constraints, and it is shown how an existing pragmatic analysis, due to Guerzoni (2007), is readily modified to explain the new judgments.