Oshima (2007) and Schwarz & Simonenko (2018a) credit the unacceptability
of so-called factive islands to necessary infelicity – the violation of some
or other felicity condition on (wh-)questions in all accessible contexts. We apply
this analysis to new types of factive islands – in wh-questions with if any and in
multiple wh-questions – and argue that they pose challenges for an analysis in terms
of necessary infelicity. We propose that factive islandhood can be understood as
due to necessary blocking: in all accessible contexts where such a question would
otherwise be felicitous, the speaker would have had to use a different, more suitable,
question instead. We show that the necessary blocking analysis applies correctly to
both classic factive islands and to the new types that we have identified
