Seismic assessment is a paramount issue and a valuable instrument towards the conservation of vulnerable structures in seismic prone regions. The past seismic events have highlighted the vulnerability of masonry towers that is exhibited by severe structural and nonstructural damages or even collapses. The preservation of existing structures, mainly focused on the built heritage, is emerging and imposing substantial enhancements of numerical methods, including pushover analysis approaches. The accuracy of the estimated seismic capacity for these structures is correlated with the assumed strategies and approximations made during the numerical modeling. The present paper concerns those aspects by exploring the limitations and possibilities of conceiving pushover analysis in the finite element method environment. The most crucial target is tracing in a pushover capacity curve the corresponding initiation of structural damages, maximum load-bearing capacity, and the ultimate displacement capacity. Different recommendations for achieving this target have been proposed and illustrated for practical utilization. Three representative geometrical towers, adopting three different materials and five different load patterns, are investigated in this study. The load pattern’s role and necessity of the displacement-like control approach for the pushover analysis are exploited. This paper highlights the load-bearing capacity overestimation when the force-controlled are implemented. The material model influences the achievement of softening branch with a distinguishable displacement capacity.