We consider the problem of length generalization in sequence prediction. We define a new metric of performance in this setting -- the Asymmetric-Regret -- which measures regret against a benchmark predictor with longer context length than available to the learner. We continue by studying this concept through the lens of the spectral filtering algorithm. We present a gradient-based learning algorithm that provably achieves length generalization for linear dynamical systems. We conclude with proof-of-concept experiments which are consistent with our theory.