There are several narratives about the empowerment of midwives and midwifery around the world, with many similarities and some differences. Some of the narratives of empowerment in countries, such as India, have a history spanning decades with several waves of foreign aids for midwifery implementation from different countries in the Global North; and with varied levels of political will and support, and secondary stakeholders changing every few years, while the primary stakeholders, the women and their midwives, remain the same through the struggles, efforts and interventions. In this chapter, the boot represents the powerful and privileged secondary stakeholders, and the neck belongs to the primary stakeholders. Through two case studies of insensitive policy making on [1] the two-finger test or virginity test for sexual violence survivors and [2] the rising rates of caesarean section, we represent the story of systemic oppression of women and midwives in sexual, reproductive and maternal health. We aim to initiate the discourse of intergenerational compassion as a potential solution to lift the boots from our necks.