Black women remain underrepresented in middle and senior-level management positions in the United States (Perry, 2023). While the term "glass ceiling" refers explicitly to the discrimination and lack of representation in executive leadership roles for women, the term "concrete ceiling" has gained traction as it applies to Black women based upon their scarcity in the C-Suite (Johnson, 2021a). The African American Women Executive (AAWE) leadership model created by Parker and Ogilvie (1996) provides a conceptual framework for understanding Black women's unique leadership context in the workplace. While diversity, equity, and inclusion (DEI) initiatives gained momentum between 2019 and 2023—driven by high-profile incidents of racial injustice and the rise of the Black Lives Matter movement—recent years have witnessed a notable retrenchment in organizational support for DEI, potentially exacerbating challenges for Black women executives. This qualitative, exploratory case study employed a phenomenological approach to investigate how shifting organizational support for DEI initiatives impacts the leadership strategies and behaviors of five Black women in C-suite positions. The study examined their lived experiences across three phases: pre-2020 baseline, the surge in DEI support following the murder of George Floyd, and the subsequent backlash marked by political and societal resistance to DEI. Findings revealed that during periods of increased DEI investment, participants reported greater access to mentorship, advocacy, and professional development. Conversely, as organizational support for DEI initiatives decreased, executives experienced feelings of isolation, increased exposure to bias, and a need for more creative risk-taking.