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"Trippe" spent the remainder of 1939 outfitting at Boston. In January 1940, she visited Newport, Rhode Island, to take on torpedoes and Yorktown, Virginia, to load depth charges before heading for the Gulf of Mexico. Following shakedown training in the Gulf of Mexico and the Caribbean, she returned to Boston on 20 March 1940. After completing her post-shakedown overhaul, "Trippe" departed Boston on 24 June ultimately to join the Caribbean portion of the Neutrality Patrol. She voyaged via Hampton Roads to San Juan, Puerto Rico, where she arrived early in July only to return north at mid-month for a two-day visit to Washington, D.C.. On 26 July, "Trippe" entered San Juan once more to begin Neutrality Patrol duty in earnest.