The standard model of particle physics provides a coherent description of highenergy physics processes and has been hugely successful in providing experimental predictions. Among its long list of achievements, the most significant is arguably that of the discovery of the Higgs boson half a century after being theorised, providing the last cornerstone needed for the standard model to become fully consistent. Despite huge successes, the standard model still suffers from major shortcomings. On the path leading towards a better understanding of particle physics, an in-depth study of the Higgs boson is key. This relentless work of characterising the properties of the Higgs boson is currently being undertaken at the Large Hadron Collider, where high-energy proton collisions are being recorded by dedicated detectors, providing a continuous improvement to the understanding of the standard model. Amid tremendous achievements, some processes, remain too weak to be detected with the current installations. One such measurement is the combined production of two Higgs bosons allowing for a direct handle on the Higgs self-coupling parameter of the standard model. To maximise the physics reach of the collider, it will be subjected to a major upgrade, allowing for a strong increase in luminosity. Such a dramatic change will bring major challenges to the experiments recording these collisions and upgrades are required if they are to maintain their outstanding performance. This thesis explores the upgrade of the CMS silicon strip detector, centred around the in-beam characterisation of detector module prototypes and discusses the physics reach of the upgraded machine, with an emphasis on Higgs boson pair production in the bbWW(l) final state.