Microwave squeezing represents the ultimate sensitivity frontier for superconducting qubit measurement. However, measurement enhancement has remained elusive, in part because integration with standard dispersive readout pollutes the signal channel with antisqueezed noise. Here we induce a stroboscopic light-matter coupling with superior squeezing compatibility, and observe an increase in the final signal-to-noise ratio of 24%. Squeezing the orthogonal phase slows measurement-induced dephasing by a factor of 1.8. This scheme provides a means to the practical application of squeezing for qubit measurement.