Writer's workshop is a popular curriculum opportunity in most US schools. This case study of two Black boys engaging in a Kindergarten writer's workshop richly contextualizes their writing identities and practices. A critical childhood studies framework was used to show how Black boys and their White teachers improvised writing-related relationships. The research questions for the study were: (1) How did Black boys use creativity and strength to push back against the semi-scripted curriculum in Kindergarten writer's workshop? (2) What can teachers and teacher educators learn from their examples? In the findings Black boys strove to think, understand, and practice writing freely and to use their personal and cultural resources outside the constraints of teaching scripts. However, when teachers did not navigate the semi-scripted curriculum, all the children were robbed of their writing identities but Black boys were most deeply affected. Reflection questions and suggestions for teacher educators and professional developers are designed to support the use of improvisational practices and African diaspora literacy in early childhood and elementary school writing contexts.