Photonic nanostructures with gain and loss have long been of interest in the context of diverse scattering anomalies and light-shaping phenomena. Here, we investigate the scattering coefficients of simple gain-doped diffractive metasurfaces, revealing pairs of scattering anomalies surrounded by phase vortices in frequency–momentum space. These result from an interplay between resonant gain, radiative loss, and interference effects in the vicinity of Rayleigh anomalies. We find similar vortices and singular points of giant amplification in angle-resolved reflectivity spectra of prism-coupled gain slabs. Our findings could be of interest for gain-induced wavefront shaping by all-dielectric metasurfaces, possibly employing gain coefficients as low as ∼50 cm−1.