We study how market design choices exacerbate or mitigate pre-existing inequalities among participants. We introduce outside options in a well-known school choice model, and show that students always prefer manipulable over strategy-proof mechanisms if and only if they have an outside option. We test for the proposed relationship between outside options and manipulability in a setting where we can identify students’ outside options and observe applications under two mechanisms. Consistent with theory, students with an outside option are more likely to list popular, highly-rated schools under the Boston mechanism, and this gap disappears after switching to a Deferred Acceptance mechanism.