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A protocol for the Cu(TFA)2‐catalyzed (TFA=trifluoroacetic acid) picolinamido‐directed C8−H cyanation of naphthalene derivatives with benzoyl cyanide as the cyano source has been developed. A series of 8‐cyano‐1‐(picolinamido)naphthalene derivatives were efficiently obtained in moderate to good yields by using this method. We prepared a total of 22 products, 10 of which have not previously been reported. Benzoyl cyanide was originally employed for the C(sp2)−H cyanation of arenes. The picolinamide moiety served a critical role as the directing group in this cyanation reaction of naphthalenes. Pick‐a‐little/Talk‐a‐little: A method for the Cu(TFA)2‐catalyzed (TFA=trifluoroacetic acid) picolinamido‐directed C8−H cyanation of naphthalene derivatives with benzoyl cyanide as the cyano source has been developed. We prepared a total of 22 products, 10 of which have not previously been reported. Benzoyl cyanide was originally employed for the C(sp2)−H cyanation of arenes. TFA=trifluoroacetic acid and DMAc=N,N‐dimethylacetamide.