Cobalt‐catalyzed anti‐Markovnikov reactions that involve siloxy‐ or alkoxy(vinyl)silanes and siloxy‐ or alkoxyhydrosilanes are disclosed. More than 25 new cobalt–(aminomethyl)pyridine complexes were developed as catalysts for the hydrosilylation of industry‐relevant and challenging siloxy‐ or alkoxy‐terminated vinylsilanes. These transformations typically proceed in the presence of 0.25 mol % of the cobalt complex with 0.75 mol % of the alkylating agent to afford the desired products in up to >98 % yield with >98 % anti‐Markovnikov selectivity in 30 min. The current protocol shows a broad substrate scope, delivering more than 25 siloxanes with siloxy or alkoxy functional groups at both termini, and can also be applied to polymeric vinyl‐ and hydrosiloxanes.