On 1 June 1885 Reynolds was promoted to second lieutenant. He remained assigned to the "Chase" until 21 April 1888. On 15 April 1889, he returned to the "Chase" for a little more than one year, leaving on 19 May 1890. On 18 January 1896 Reynolds was promoted to first lieutenant. Coincidentally, on that same date, the court-martial of Captain Michael "Hell Roaring Mike" Healy for conduct unbecoming of an officer and hazarding the safety of his vessel, the USRC "Bear", by being intoxicated; began in San Francisco, California, and Reynolds had been appointed as prosecuting officer. He was successful and Healy was convicted on all charges on 5 March 1896.