Dielectric metasurfaces supporting Mie resonances can allow significantly boosted and tailored nonlinear light–matter interactions at the nanoscale. However, nonlinear dielectric metasurfaces typically only have odd‐order nonlinearities, unless resorting to material systems such as GaAs, GaP, or LiNbO3, each with unique challenges in device fabrication and integration. As the most widely adopted constituent material of metasurfaces, silicon (Si) does not possess an intrinsic second‐order nonlinear susceptibility. Herein, second‐harmonic generation (SHG) in a Si metasurface strained by a silicon nitride (SiN
x
) cladding layer is demonstrated. Utilizing the stress caused by the SiN
x
layer to break the inversion symmetry of the bulk Si crystal, greatly enhanced SHG in the strained Si metasurface compared with that from an unpatterned Si film with the SiN
x
cladding layer, with an experimentally measured conversion efficiency as high as 4.2 × 10−5 W−1, is observed. Experiments are further performed and it is concluded that the enhanced SHG is most likely due to the applied stress instead of charged defects in the SiN
x
cladding. This work opens a new route to realizing dielectric metasurfaces with second‐order nonlinearity in a complementary metal–oxide–semiconductor (CMOS)‐compatible platform.