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This paper examines how new ventures navigate asymmetrical collaborations with incumbents, focusing on the post-pilot commercialization phase. While these collaborations offer critical resources, they trap ventures in prolonged pilot projects that often fail to translate into commercial impact. We argue that this dynamic gives rise to a “bear hug” dilemma, wherein a firm becomes increasingly constrained by asymmetric relational dependence. Using a qualitative multiple case study of ten Swedish digital technology startups, we outline divergence in post-pilot commercialization trajectories, each guided by a sequence of contingencies that determine a startup’s collaboration engagement strategy. Importantly, we show that small firms navigate this dilemma not always by trying to “escape” bear hugs; instead, they may seek to “tame” them by deliberately deepening relational dependence. Overall, this study shifts attention from how to secure and protect against asymmetric partnerships to how to convert them into actual commercial opportunities.