We carry out simple analytical calculations and Monte Carlo studies to better understand the impact of QCD radiation on some well-known jet substructure methods for jets arising from the decay of boosted Higgs bosons. Understanding differences between taggers for these signal jets assumes particular significance in situations where they perform similarly on QCD background jets. As an explicit example of this we compare the Y-splitter method to the more recently proposed Y-pruning technique. We demonstrate how the insight we gain can be used to significantly improve the performance of Y-splitter by combining it with trimming and show that this combination outperforms the other taggers studied here, at high . We also make analytical estimates for optimal parameter values, for a range of methods and compare to results from Monte Carlo studies.