Armstrong was a 1965 graduate of Hattiesburg's Royal Street High School. She wished to attend college but had to stay at home to care for her invalid mother. The NAACP offered to support her entry into the local segregated white university, and recruited local civil rights activist Raylawni Branch to enter with her as moral support. This required considerable physical courage for both, but especially the inexperienced 18-year-old Armstrong. Having grown up in the black community of Hattiesburg, she was well aware of the notorious miscarriage of justice in which the last black to attempt to enroll at the university had been falsely sent to prison and an early death. By this time both Ole Miss and Mississippi State University had been integrated – the former violently, the latter peacefully. The Mississippi State Sovereignty Commission and University of Southern Mississippi leaders, such as President Dr. William David McCain, had earlier fought vociferously and successfully to thwart Clyde Kennard's attempts to enroll at Mississippi Southern College. They had now come to realize that the battle to maintain segregation was lost. Therefore, McCain and his staff made extensive confidential plans for the admission and attendance of Armstrong and Branch. A faculty guardian and mentor was secretly appointed for each. The same campus police department which in 1959 had attempted to railroad Kennard to prison when he attempted to enroll, now had very strict orders to prevent or quickly stop any incident involving the two black students. Student athletic, social, and political leaders were recruited to keep the calm and protect the university from such bad publicity as Ole Miss had suffered from its reaction to James Meredith. As a result, Armstrong had only very minor negative experiences. She studied music and singing, and helped the university choir win a championship. According to Branch, they were "treated just like everybody else.". In 1968 Armstrong pursued a brief career as a jazz styled singer recording in Nashville for a release on King Records. The two women were accompanied by six bodyguards when on campus. The university administration appointed Dr. Geoffrey Fish, an oceanographer who taught biology as her guardian and tutor. Fish took a genuine interest in both women, gave them advice and jobs in work-study. He was very kind, listened to them, and was like a father figure to them.
