The value at risk (VaR) and the conditional value at risk (CVaR) are two popular risk measures to hedge against the uncertainty of data. In this paper, we provide a computational toolbox for solving high-dimensional sparse linear regression problems under either VaR or CVaR measures, the former being nonconvex and the latter convex. Unlike the empirical risk (neutral) minimization models in which the overall losses are decomposable across data, the aforementioned risk-sensitive models have nonseparable objective functions so that typical first order algorithms are not easy to scale. We address this scaling issue by adopting a semismooth Newton-based proximal augmented Lagrangian method of the convex CVaR linear regression problem. The matrix structures of the Newton systems are carefully explored to reduce the computational cost per iteration. The method is further embedded in a majorization–minimization algorithm as a subroutine to tackle the nonconvex VaR-based regression problem. We also discuss an adaptive sieving strategy to iteratively guess and adjust the effective problem dimension, which is particularly useful when a solution path associated with a sequence of tuning parameters is needed. Extensive numerical experiments on both synthetic and real data demonstrate the effectiveness of our proposed methods. In particular, they are about 53 times faster than the commercial package Gurobi for the CVaR-based sparse linear regression with 4,265,669 features and 16,087 observations. History: Accepted by Antonio Frangioni, Area Editor for Design & Analysis of Algorithms–Continuous. Funding: This work was supported in part by the NSF, the Division of Computing and Communication Foundations [Grant 2153352], the National Natural Science Foundation of China [Grant 12271187], and the Hong Kong Research Grant Council [Grant 15304019]. Supplemental Material: The software that supports the findings of this study is available within the paper and its Supplemental Information ( https://pubsonline.informs.org/doi/suppl/10.1287/ijoc.2023.1282 ) as well as from the IJOC GitHub software repository ( https://github.com/INFORMSJoC/2022.0012 ) at ( http://dx.doi.org/10.5281/zenodo.7483279 ).