Dislocation-obstacle interactions are well established as an effective strengthening and hardening mechanism within metallic materials. Due to these desirable characteristics, dislocation-obstacle interactions have been the subject of study for decades. Despite previous efforts, quantitative relationships between obstacle size, shape, density, distribution, and increased strengthening and hardening remain elusive. Within this talk, we present our recent efforts towards quantifying the influence of dislocation- obstacle interactions on material strengthening. Our efforts include (i) mechanistic analyses of the Orowan bypass stress around a row of ellipsoidal, impenetrable obstacles, (ii) simulations of dislocation glide through random distributions of obstacles, and (iii) statistical analyses of the same problem. Collectively, our simulations and analyses provide quantitative relationships between obstacle size, shape, density, and distribution and metallic strengthening mechanisms.