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The Negro Motorist Green Book was a tool used by the Black community to navigate systemic racism throughout the U.S. and around the world. Whether providing its users with safer roads to take or businesses that were welcoming to Black patrons, The Negro Motorist Green Book fostered pride and created a physical network of safe spaces within the Black community. Building a bridge between this artifact which served Black people for thirty years and the current moment, we explore Black Twitter as an online space where the Black community navigates identity, activism, racism, and more. Through interviews with people who engage with Black Twitter, we surface the benefits (such as community building, empowerment, and activism) and challenges (like dealing with racism, appropriation, and outsiders) on the platform, juxtaposing the Green Book as a historical artifact and Black Twitter as its contemporary counterpart. Equipped with these insights, we make suggestions including audience segmentation, privacy controls, and involving historically disenfranchised perspectives into the technological design process. These proposals have implications for the design of technologies that would serve Black communities by amplifying Black voices and bolstering work toward justice.