In this work, a broadband stripline-to-rectangular waveguide transition is presented. It uses a rectangular-shaped probe to couple the energy from rectangular waveguide to stripline. The two ground planes of the stripline are extended for field matching of the transition. A back-to-back transition prototype at Ka-band is designed, fabricated and measured. The measured results show that the transition has less than 1.2 dB insertion loss and better than 15 dB return loss over the frequency range from 26.5 to 40 GHz. The 15 dB fractional bandwidth is increased from 11.6 to 41% compared with conventional stripline-to-waveguide transition. The measured results agree well with simulated ones.