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On August 4, 2021, Illinois Governor Pritzker issued his 85^th COVID-related executive order, mandating face masks for all Pre-K through 12^th grade schools throughout Illinois, both private and public. This new mandate, applicable to students, teachers, and other School personnel, has raised many questions and objections. For instance, is this new government mandate legally enforceable? Should it be followed regardless of its potential legal invalidity, particularly given the fluidity of medical, legal, and other important considerations? Could any mask exemptions apply, such as based on a student’s or staff member’s health condition or right of conscience objection? This article navigates through these challenging questions, with potentially available options and related recommendations.