Manuel, Simon, I've spotted a hopefully small but for us quite annoying bug in GHC's type checker: it loops when overloading resolving involves a circular constraint graph containing type-family applications. The following program (also attached) demonstrates the problem: {-# LANGUAGE FlexibleContexts #-} {-# LANGUAGE TypeFamilies #-} type family F a :: * type instance F Int = (Int, ()) class C a instance C () instance (C (F a), C b) => C (a, b) f :: C (F a) => a -> Int f _ = 2 main :: IO () main = print (f (3 :: Int)) My guess is that the loop is caused by the constraint C (F Int) that arises from the use of f in main: C (F Int) = C (Int, ()) <= C (F Int) Indeed, overloading can be resolved successfully by "black-holing" the initial constraint, but it seems like the type checker refuses to do so. Can you confirm my findings? I'm not sure whether this is a known defect. If it isn't, I'd be more than happy to issue a report. Since this problem arises in a piece of very mission-critical code, I would be pleased to learn about any workarounds. Thanks in advance, Stefan