Tunable halofluoroalkylation and hydrofluoroalkylation of 1,6‐enynes were first reported by switching between copper‐catalysis and photocatalysis, leading to the atom‐economic and highly stereoselective protocols toward functionalized 1‐indenones with moderate to good yields. Copper‐catalysis enabled the concomitant incorporation of two important fluoroalkyl and halo functionalities into 1‐indenone skeleton, in which fluoroalkyl bromides were transformed into (E)‐1‐indenones as a major stereoisomer while fluoroalkyl iodides oriented complete Z‐selectivity to access (Z)‐1‐indenones. Specifically, photocatalysis allowed hydrofluoroalkylation of 1,6‐enynes to access fluoroalkylated (Z)‐1‐indenones under mild conditions, in which THF behaved as a hydrogen source. These two approaches feature remarkable compatibility with a wide variety of 1,6‐enynes and fluoroalkyl halides and excellent atomic utilization.