  In this paper we investigate the hadronic mass spectra of inclusive B decays.
Specifically, we study how an upper cut on the invariant mass spectrum, which
is necessary to extract V_{ub}, results in the breakdown of the standard
perturbative expansion due to the existence of large infrared logs. We first
show how the decay rate factorizes at the level of the double differential
distribution. Then, we present closed form expressions for the resummed cut
rate for the inclusive decays B -> X_s gamma and B -> X_u e nu at
next-to-leading order in the infrared logs. Using these results, we determine
the range of cuts for which resummation is necessary, as well as the range for
which the resummed expansion itself breaks down. We also use our results to
extract the leading and next to leading infrared log contribution to the two
loop differential rate. We find that for the phenomenologically interesting cut
values, there is only a small region where the calculation is under control.
Furthermore, the size of this region is sensitive to the parameter
\bar{\Lambda}. We discuss the viability of extracting V_{ub} from the hadronic
mass spectrum.
