Previous studies concluded that despite the parser’s eagerness to resolve filler-gap dependencies, in island configurations it prefers to posit late grammatical gaps over early ungrammatical ones. This study investigates the possibility of resolving filler-gap dependencies inside Hebrew islands. We investigated the acceptability of resumptive pronouns (RPs) in two islands and the sensitivity of on-line dependency formation to the status of those RPs. Results revealed a filled-gap effect inside the island that allows RPs but not inside the one that prohibits them. This suggests that active dependency formation can proceed inside islands, and that when processing dependencies with islands, the Hebrew parser prefers an early RP over a later gap.