In "Little Rock School District v. North Little Rock School District", No. 04-2923 (2006), Gruender opposed the opinion of a panel of the Eighth Circuit that affirmed the district court's conclusion that federal desegregation monitoring should remain in effect in Little Rock, Arkansas. After the desegregation effort of the Little Rock Nine in 1957, the federal government began monitoring the school district in 1965. The Eighth Circuit agreed with the district court that the Little Rock district did not successfully evaluate its academic programs for how well they helped black students. Gruender dissented, arguing that the district court abused its discretion in mandating federal monitoring by using "impossibly subjective" criteria. The district court subsequently agreed with Gruender's reasoning and freed the school district from federal desegregation monitoring. In 2009, the Eighth Circuit then upheld the district court's decision in another appeal, No. 07-1866.