This paper details four encounters we experienced while traveling in Cuba as part of a multiethnic delegation of US social justice advocates. The encounters were linked by a common thread of race, which made them noteworthy and uncomfortably familiar to us as Black women. Since our return to the US, we have reflected on the four encounters and concluded that, as a collective, they reinforce a lesson and highlight a fundamental challenge that is at the core of the work of all critical multicultural and social justice educators.