This comment analyzes the current state of students' free speech rights in the context of creative writing assignments and examines potential First Amendment applications to the Pennsylvania System of School Assessment (PSSA), a statewide, mandatory, standards-based exam administered to Pennsylvania public school students. The PSSA, which currently contains a writing assessment for students in sixth, ninth, and eleventh grades requiring students to write essays in response to prompts, is scored anonymously by private entities under contract with the Pennsylvania Department of Education. Those private subcontractors have "red-flagging" procedures in place to identify essays containing imagery or themes that indicate imminent threats of harm to the writer or to others. Red-flagged essays are matched with the name of the writer and are sent to local school officials. This comment examines the red-flagging procedure and offers suggestions for ensuring that students, teachers, administrators, and parents are made aware of how the education system in general and PSSA officials in particular are attempting to protect not only the safety of the community but also students' rights of creativity and free expression.