A convenient approach for synthesizing indole‐N‐carboxamide derivatives through palladium‐catalyzed isocyanide insertion into the N‐H bond of 3‐(phenylhydrazono)oxindoles has been developed. The inclusion of the 3‐phenylhydrazone group proved essential in remotely activating the N‐H bond of the oxindole. Also, it has been established that the reaction outcome is highly dependent on the electronic effects of the substituents.