A highly regio- and stereoselective copper-mediated cyanodifluoroalkylation of alkynes with ethyl difluoroiodoacetate and trimethylsilyl cyanide (TMSCN) is described. The three-component coupling reaction provides straightforward access to a variety of useful difluoroalkyl-substituted acrylonitriles. The introduction of the nitrile unit is of great importance in drug discovery for the modification of this fragment. Preliminary mechanistic investigations indicate that a vinyl iodide intermediate and a difluoroalkyl radical might be involved in this transformation.