Drawing largely on the work of Maya Angelou, we use decolonial collaborative autoethnography to explore why the caged bird sings in the academy. We offer a "caged bird sings" framework based on Angelou's book and use it to analyze our autoethnographic performances. What we found through this work is that the legacy of colonialism in the academy continues to serve as a cage, but within that cage, we, as African American and Puerto Rican faculty and staff, continue to find ways to sing. Moreover, our song helps us at times to survive and other times to thrive. The biggest tragedy is to not sing at all, leaving the cage unchallenged.