The high‐power characteristic of the coaxial to waveguide transition plays an important role in modern communication and radar systems. In this letter, a novel design of a high‐power transition from a 50 Ω coaxial line with an N‐type connector to a WR‐90 rectangular waveguide. The power handling capability (PHC) of the proposed structure is significantly enhanced by a cone‐shaped excitation probe with a bold end, a transitional cavity, and a mode conversion cavity with a curved shorted back wall. The simulated results reveal that the transition possesses high PHC of 257 kW at 8.5 GHz, which is the upper limit of the power tolerance for the N‐type connector. The measured results show that the return loss and insertion loss are better than 15 and 0.15 dB, respectively, in the range of 7.96–9.16 GHz. In addition, experimental validation confirms the normal operation of the structure under a 250 kW power level test, demonstrating the applicability of the proposed transition in high‐power microwave systems.