This fails, saying nil requires a type annotation, but without the lambda it works, so the lambda isn't propagating the expected type:
(define (expect-→listof-int [f : (→ (List Int))] → Int)
0)
(check-type (expect-→listof-int (λ () nil)) : Int -> 0)
The pull request https://bitbucket.org/stchang/macrotypes/pull-requests/9 fixes this issue.