In 1974, Cutler moved to Alaska to work as a research attorney for the Alaska Judicial Council.[3] She then went to work as a public defender.[3][6] Cutler was appointed by Governor Jay Hammond as a district court judge in Anchorage, Alaska and was sworn in on September 26, 1977.[6][3][1] At 28 years old, she replaced Dorothy Tyner, who was much older.[6][3][1] When first appointed to the bench, Cutler was the only judge in a one-courtroom courthouse.[1] As the court grew, they expanded into a nearby apartment where files were kept in the bathtub.[2]
In 1982, she was appointed the first judge at what is, as of 2012, the Superior Court in Palmer.[3] When she became a superior court judge there was no district court in that jurisdiction, and so the duties of that role were Cutler's as well.[2]
She received criticism after John Pearl Smith II, a prisoner she temporarily released to attend his deceased father's memorial service, escaped and was later recaptured.[1] She also presided over a case involving the mother of Levi Johnston.[5]
Cutler retired in 2009 after spending 32 years as a judge.[1][3] She was also the superior court's administrative judge.[2] At the end of her career, she served alongside three other judges in Palmer, Alaska, where she presided for 27 years.[1]