This paper deals with wh-in situ elements (i.e. wh-elements that stay in the argument position) in islands such as adverbial clauses, conditionals, relative clauses, complement clauses, etc. extracted from corpora of Italian and Spanish. I will show that there are two types of wh-in situ embedded inside an island in these languages. One type is a real genuine question. Another type is an echo question. There are several approaches that convincingly account for the insensitivity of echo questions to islands. The genuine question type is still a puzzle for semantic and syntactic approaches. It turns out that wh-in situ questions with a genuine question interpretation are only possible inside islands that are not marked for sentence type and do not contain any operator that could block the question interpretation of the wh-in situ. This way question alternatives can be passed higher up the clause until they meet a question operator in the matrix clause that interprets them. Consequently, the question is well-formed and interpreted without any problem. Real islands contain semantic operators or quantifiers that interpret question alternatives triggered by wh-in situ until they reach the question morpheme to be interpreted as question alternatives. The result is that the derivation crashes.