This thesis contains the work of two recent developments in the Herwig general purpose event genrator. Firstly, the results from an new implementation of the KrkNLO method in the Herwig event generator are presented. This method allows enables the generation of matched next-to-leading order plus parton shower events through the application of simple positive weights to showered leading order events. This simplicity is achieved by the construction Monte Carlo scheme parton distribution functions. This implementation contains the necessary components to simulation Drell-Yan production as well as Higgs production via gluon fusion. This is used to generate the first differential Higgs results using this method. The results from this implementation are shown to be comparable with predictions from the well established approaches of POWHEG and MC@NLO. The predictions from KrkNLO are found to closely resemble the original configuration for POWHEG. Secondly, a benchmark study focussing on the source of perturbative uncertainties in parton showers is presented. The study employs leading order plus parton shower simulations as a starting point in order to establish a baseline set of controllable uncertainties. The aim of which is to build an understanding of the uncertainties associated with a full simulation which includes higher-order corrections and interplay with non- perturbative models. The uncertainty estimates for a number of benchmark processes are presented. The requirement that these estimates be consistent across the two distinct parton show implementations in Herwig provided an important measure to assess the quality of these uncertainty estimates. The profile scale choice is seen to be an important consideration with the power and hfact displaying inconsistencies between the showers. The resummation profile scale is shown to deliver consistent predictions for the central value and uncertainty bands.