In April 1969 the U.S. 5th Circuit Court of Appeals ruled that the desegregation plan adopted by the Indianola Municipal Separate School District was unconstitutional.

[3] So-called "white flight" followed, with an overwhelming percentage of the white students of Indianola enrolled at Indianola Academy, a segregation academy which, as a private school, was not subject to federally mandated desegregation.

[6] Sarah Carr of The Atlantic said "Compared to Indianola Academy, Gentry High School is an open book, its academic struggles exposed to the world" and that "Gentry has struggled with test scores since the state's accountability system began in the 1990s.

"[6] The school uses paddling, a form of corporal punishment, to correct student misbehavior.

In 2012 Earl Watkins, the conservator appointed by the State of Mississippi to oversee the Indianola School District, said that "Because corporal punishment has been a practice for many years in the district, professional development must precede the reduction/phase-out of it.

"[6] Apolonio said that the lack of resources contributes to the discipline issues, explaining that "During the winter it gets cold and the heaters don't work in the classrooms.

According to Gentry employees, five left after one year because, as paraphrased by Carr, "for personal reasons, or because of frustration with the job.