Pipelines are technological and political undertakings, but also financial feats. When pipelines are in protracted states of uncertainty—not yet built, but not yet canceled—the outcomes seem not to benefit anyone: proponents face cost overruns and regulatory battles, while potentially affected communities remain under threat of disruption and dispossession. In light of these negative outcomes, why do such projects remain in liminal states for so long? To answer this question, we interrogate two contested oil pipeline proposals in Canada, the Northern Gateway Pipelines and the Trans Mountain Expansion projects. In both cases, we find that the complex and shifting financial arrangements for these pipelines produced what we call ‘contested assetization.’ This process operates through three intertwined dynamics: temporality (collapsing and expanding time), market valuation (specific forms of knowledge and professional practices), and financial tools (contractual, equity, and other financial arrangements). Proponents create complex, layered future-oriented investable assets, mediating corporate risk; at the same time, opponents target multiple regulatory venues, challenge valuation systems, and highlight future social and ecological costs. We find that although the strategic use of these dynamics has contradictory consequences, overall, these financial processes reinforce corporate power, prolonging fossil fuel-based energy futures.