Directly measuring the Higgs self-coupling through Higgs pair production is an active area of interest for the LHC experiments, with a current limit around 10 times the Standard Model cross section per experiment. These results, exploting early Run 2 LHC data, show that a much larger dataset will be needed for discovering the Standard Model HH production process. A summary of the prospects of the sensitivity of these analyses utilizing the High-Luminosity LHC dataset is presented. Different strategies for obtaining these results are discussed, along with the most important challenges these analyses will face in the future. A combination of the ATLAS and CMS prospected sensitivities is also presented.