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The nonlinear dynamics of propellant sloshing during orbital ascent are usually neglected in the flight control analysis of large boost vehicles under the assumption that the viscous damping of the fluid is sufficient to suppress nonlinear phenomena and confine the fluid to small, planar free surface displacements. In this case, the sloshing dynamics can be modeled using a spring-mass-damper or linearized pendulum mechanical analog. However, large, smooth-wall tanks without significant internal hardware or ring baffles are still susceptible to nonlinear effects. In particular, rotary sloshing can present a risk to flight control as it involves the formation of a stable limit cycle which can lead to undesirable roll coupling. The underlying phenomena of jump resonance does not manifest in linear models, but can be reproduced using a nonlinear spherical pendulum or the Bauer paraboloid model developed during the Apollo/Saturn program. In this paper, a detailed analysis of the rotary sloshing dynamics of these mechanical analogs is presented, and discussed in the context of flight control stability. High-fidelity simulations of a representative boost vehicle are used to verify the semi-analytical predictions of the nonlinear dynamic response.