Asymmetry issues between partners concern the complementarity of assets across firms differing substantially in size, origin, experience, and objective, for which scholars highlight the importance of digital technologies (DTs) and learning. However, factors that influence partners to invest in DTs and learning remain underexplored. This study investigates how the collaborative context (complementarity, commitment, and compatibility) of asymmetric alliances affect the decision to digitise to enhance learning. We use six case studies of asymmetric alliances between partners from an emerging market and developed markets operating in varied sectors. The study reveals the types of collaborations under which partners can exploit DTs to develop learning capabilities. It also offers an adapted framework for such collaborations in the aspects of complementarity (absorptive capacity), compatibility (organisational culture and reciprocity), and commitment (objectivity and stability of the alliance). The results underline that high collaboration motivates partners to invest in digital platforms, leading to joint learning.