Organizational and target contexts are antecedents of deliberate learning from mergers and acquisitions. We consider strategic orientations (market vs. entrepreneurial orientation) of firms as important organizational contexts driving knowledge codification behavior. Further, we argue that the similarity of target context (“in the market” vs. “out of the market”) is an important contingency factor in this relationship. The hypotheses of this study are tested using survey data from 115 acquirers in manufacturing industries from Austria, Germany, and Switzerland. The results provide insights into organizational learning mechanisms from previous acquisition activities. Entrepreneurial and market-oriented firms differ concerning their codification behavior. Market-oriented firms generally engage more in knowledge codification. Further, although market-oriented acquirers focus on knowledge codification from similar contexts (“in the market” targets), entrepreneurial-oriented acquirers focus on knowledge codification from heterogeneous contexts (“out of the market” targets). The results are discussed in-depth and theoretical and managerial implications are derived.