This paper addresses the challenges and limitations involved in the measurement of steep freeform wavefront by using Shack-Hartmann Sensor (SHS). To estimate the slope errors, Zemax simulation tool is used to design a SHS setup including array of lenslets and detector plane with predefined specifications. In first step, error due to approximation of tilted plane wavefront over curved wavefront is simulated. Plane, tilted, curved and tilted-curved wavefronts are defined using appropriate ray source objects. The centroids of the focal spots of lenslets are calculated based on the detector data obtained by using ray tracing method, which is done by an in-plane scanning aperture for segmented local wavefronts sequentially.The scanning aperture is used to block rays from more than one lenslet array. Centroids from the focus spots are calculated and the slopes are estimated with respect to collimated reference wavefront for each ray trace process. Further, matrix of slope errors is used as an input for MATLAB routines for surface reconstruction and error estimation. Based on the simulation data, it is found that the assumption used in Shack-Hartmann wavefront measurement introduce residual errors. For example a 50 wave peak to valley input and 1.19 mm thick lenslet array can give up to 9 waves of residual form error. However, very thin lenslets can have very less residual error.The effect of shift of focal plane, tilted plane wavefront and curve wavefront during the reconstruction using SHS is reported.