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Wollman was nominated by President Ronald Reagan on June 25, 1985, to the United States Court of Appeals for the Eighth Circuit, to a new seat created by 98 Stat. 333. South Dakota senior senator Larry Pressler worked with the White House to secure this nomination, and recommended Wollman as a conservative judge. He was the first South Dakotan on that court in 25 years. Wollman was confirmed by the United States Senate on July 19, 1985, and he received his commission on July 22, 1985. From 1999 to 2002, Wollman served as Chief Judge. Wollman maintains his chambers in Sioux Falls, South Dakota.
On February 9, 2018, Wollman notified President Donald Trump that he intended to step down as an active judge no later than the end of 2018. He assumed senior status on December 14, 2018, upon the confirmation of his successor and former clerk, Jonathan A. Kobes. Wollman assumed inactive senior status in September 2024.