The IT industry provides supportive pathways such as returnship programs, coding boot camps, and buddy systems for women re-entering their job after a career break. Academia, however, offers limited opportunities to motivate women to return. We propose a diverse multicultural research project investigating the challenges faced by women with software engineering (SE) backgrounds re-entering academia or related research roles after a career break. Career disruptions due to pregnancy, immigration status, or lack of flexible work options can significantly impact women's career progress, creating barriers for returning as lecturers, professors, or senior researchers. Although many companies promote gender diversity policies, such measures are less prominent and often under-recognized within academic institutions. Our goal is to explore the specific challenges women encounter when re-entering academic roles compared to industry roles; to understand the institutional perspective, including a comparative analysis of existing policies and opportunities in different countries for women to return to the field; and finally, to provide recommendations that support transparent hiring practices. The research project will be carried out in multiple universities and in multiple countries to capture the diverse challenges and policies that vary by location.