Emails feel like private, confidential communications. But in the workplace, employers often retain the right to monitor every communication sent or received by an employee on an employer-owned device or network. This Note addresses the issue of whether attorney-client privilege should attach to communications made between an employee and her private attorney over a system monitored by her employer. When addressing this issue, most district and state courts apply a test that seeks to determine the reasonableness of the employee’s expectation of confidentiality in the attorney-client communication. However, courts differ in how they apply the expectation of reasonableness test, with nearly every court finding a different fact dispositive. This Note argues that attorneys, employers, and courts should instead use a three-pronged approach: first, attorneys should seek to prevent monitored communications with their clients from occurring in the first place; second, employers should take precautions to prevent their employees’ attorney- client communications from becoming nonconfidential; and third, courts should allow attorney-client privilege to attach to communications that the client believed were confidential. This three-pronged approach is consistent with the doctrine&rsquols other exceptions to a strict confidentiality requirement and realigns attorney-client privilege with its public policy goals.