Knowledge management (KM) programs, processes, and technology continue to top the list of business challenges for TSIA’s support services members. But according to the results of the 2021 Knowledge Management Survey, the eighth annual survey conducted on this topic by TSIA, progress toward KM maturity has stalled. Though there were a few bright spots, including a rise in average knowledge culture score, increased adoption of some innovative tools, and a slight increase in dedicated KM staffing, in general, progress in key areas such as mobility, video, and executive oversight saw flat year-over-year results and some decreases. This report will focus on both the gains and the stalls in KM progress and give some insight into challenges faced by B2B companies trying to push the Sisyphean boulder of KM up an ever-steeper hill.