Drawing upon prior research suggesting inertia prevents organizations from learning, we suggest that the relationship between entrepreneurial orientation (EO) and strategic learing (SL) is not as straightforward and linear as has been suggested. The size and age of an organization, considered indicators of inertia, are important factors affecting how EO contributes to the components of SL. Data from 182 software companies confirm the non-linear relationships between EO and the dissemination, interpretation, and implementation components vo SL. The results also indicate that the U-shaped association between EO and specific components of SL is more pronounced for larger and established companies than for younger and smaller ones. These findings depart from previous work based on strategic learning from mistakes, and offer a specific understanding of the relationship between EO and the four distinct components of SL. These results suggest that companies shoult opt to facilitate the individual components of SL as they are affected differently depending on the level of EO, and the age and size of the organization.