The album title refers to a trip that Akinmusire took to his hometown of Oakland, California in 2016, during which he witnessed the changes caused by gentrification.

The local population substantially changed due to the expansion of Silicon Valley, and long-term, often impoverished residents were driven out of the city.

"[12] The album contains eleven compositions by Akinmusire, which he recorded with his quartet consisting of pianist Sam Harris, bassist Harish Raghavan, and drummer Justin Brown.

"[13] Steve Futterman of The New Yorker commented, "The trumpeter Ambrose Akinmusire insures that the joys and the anxieties of current African-American life stay at the forefront of his aesthetic through written statements and spoken-word collaborations.

"[14] Jazzwise included On the Tender Spot of Every Calloused Moment in its list of the best new jazz albums, stating "Ambrose Akinmusire’s fifth studio album finds the 38 year-old trumpeter in as reflective a mode as ever, asking questions about black identity and avoiding clichéd pathways just as he opts for musical roads less travelled.