A circular drop is a linearly stable solution for the buoyancy-driven motion of drops in a Hele-Shaw cell [Gupta et al. J. Colloid Interface Sci. 218(l), 338 (1999)]. In the absence of surface-active agents, an initially prolate drop always goes to a steady circular shape while initially oblate drops exhibit complex dynamics [Gupta et al. J. Colloid Interface Sci. 222,107 (2000)]. In this study, the effect of insoluble surfactant impurities on the critical conditions for drop breakup is explored by using the Langmuir adsorption framework in conjunction with a physically based expression for the depth-averaged tangential stress exerted on a two-phase interface in a Hele-Shaw cell. It is shown that the presence of surfactants can have both a stabilizing and a destabilizing effect on the shape of the drop, depending on the Bond number, the magnitude of the initial perturbation, and the strength of surface convection. Similar to the clean drop dynamics, two marginally stable branches are found. Increasing the surface Peclet number results in the stabilization of the main branch while the secondary branch shifts to higher Bond numbers. The mode of breakup is also found to be strongly influenced by the strength of surface convection.