Differentiable programming techniques are widely used in the community and are responsible for the machine learning renaissance of the past several decades. While these methods are powerful, they have limits. In this short report, we discuss a common chaos based failure mode which appears in a variety of differentiable circumstances, ranging from recurrent neural networks and numerical physics simulation to training learned optimizers. We trace this failure to the spectrum of the Jacobian of the system under study, and provide criteria for when a practitioner might expect this failure to spoil their differentiation based optimization algorithms. * Equal contribution 2 Up to numerical precision, though see [Chow and Palmer, 1992, Kachman et al., 2017] for cases where the gradients will be close.Preprint. Under review.