In this paper we consider two weight bump conditions for higher order commutators. Given b and a Calderón-Zygmund operator T , define the commutator, and for m ≥ 2 define the iterated commutator]f . Traditionally, commutators are defined for functions b ∈ BM O, but we show that if we replace BM O by an oscillation class first introduced by Pérez [31], we can give a range of sufficient conditions on a pair of weights (u, v) for T m b : L p (v) → L p (u) to be bounded. Our results generalize work of the first two authors in [10], and more recent work by Lerner, et al. [28]. We also prove necessary conditions for the iterated commutators to be bounded, generalizing results of Isralowitz, et al. [20].