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The Iranian entrepreneurial ecosystem has grown dramatically during the past decade. Several improvements have been made at different levels, and, therefore, one could witness its unique achievements. Digital entrepreneurs are an integral part of this ecosystem, as most of the early achievements are the results of their proactive behaviors. Hopefully, the number of female digital entrepreneurs has increased, and their entrepreneurial activities have profoundly changed the competition scene. Therefore, this chapter provides a better understanding of the multilayered entrepreneurial ecosystem of Iran and then elaborates how female entrepreneurs are positioned in this ecosystem. Moreover, six well-known award-winning female digital entrepreneurs are introduced, and their challenges are scrutinized accordingly through narrative research. Finally, the chapter concludes with some remarks and directions for future research.