A straightforward method for the synthesis of highly functionalized vinylarenes through palladium‐catalyzed, norbornene‐mediated CH activation/carbene migratory insertion is described. Extension to a one‐pot procedure is also developed. Furthermore, this method can also be used to generate polysubstituted bicyclic molecules. The reaction proceeds under mild conditions to give the products in satisfactory yields using readily available starting materials. This is a Catellani–Lautens reaction that incorporates different types of coupling partners. Additionally, this reaction is the first to demonstrate the possibility of combining Pd‐catalyzed insertion of diazo compounds and Pd‐catalyzed CH activation. Activate and move! A novel method for the synthesis of highly functionalized vinylarenes through palladium‐catalyzed, norbornene‐mediated CH activation/carbene migratory insertion is developed under mild reaction conditions with readily available starting materials (see scheme). This is a Catellani–Lautens reaction with a diazo compound as a nucleophilic coupling partner. This unique transformation is also the first example of incorporation of CH activation in the Pd‐catalyzed insertion of a diazo compound.