Background: Exploring the ambidexterity literature in the context of agile software development organizations from the perspective of how the organizational characteristics that result from the application of agile methods affect the achievement of ambidexterity Aim: To gain insight into how agile software development organizations achieve ambidexterity. Methodology: How agile software development organizations achieve ambidexterity was studied through a multiple case study where the total of four case projects in two different organizations were examined. Findings: This study indicated how the characteristics of agile software development organizations have an essential role in how ambidexterity is achieved in these organizations.