The data taken in Run II at the Large Hadron Collider have started to probe Higgs boson production at high transverse momentum. Future data will provide a large sample of events with boosted Higgs boson topologies, allowing for a detailed understanding of electroweak Higgs boson plus two-jet production, and in particular the vector-boson fusion mode (VBF). We perform a detailed comparison of precision calculations for Higgs boson production in this channel, with particular emphasis on large Higgs boson transverse momenta, and on the jet radius dependence of the cross section. We study fixed-order predictions at next-to-leading order and next-to-next-to-leading order QCD, and compare the results to NLO plus parton shower (NLOPS) matched calculations. The impact of the NNLO corrections on the central predictions is mild, with inclusive scale uncertainties of the order of a few percent, which can increase with the imposition of kinematic cuts. We find good agreement between the fixed-order and matched calculations in non-Sudakov regions, and the various NLOPS predictions also agree well in the Sudakov regime. We analyze backgrounds to VBF Higgs boson production stemming from associated production, and from gluon-gluon fusion. ... mehrAt high Higgs boson transverse momenta, the ∆yjj and/or mjj cuts typically used to enhance the VBF signal over background lead to a reduced efficiency. We examine this effect as a function of the jet radius and using different definitions of the tagging jets. QCD radiative corrections increase for all Higgs production modes with increasing Higgs boson pT, but the proportionately larger increase in the gluon fusion channel results in a decrease of the gluon-gluon fusion background to electroweak Higgs plus two jet production upon requiring exclusive two-jet topologies. We study this effect in detail and contrast in particular a central jet veto with a global jet multiplicity requirement.