The Cook County Assessor’s Office (Assessor’s Office) has been recognized with a 2021 Achievement Award from the National Association of Counties (NACo) for its work in moving its paper-driven operations onto more user-friendly digital platforms. Up until 2020, the assessment of more than 1.9 million parcels still relied heavily on paper applications and forms. For the first time in the history of the Assessor’s Office, applications for both property tax exemptions and assessment appeals were fully accessible online. Under the leadership of Cook County Assessor Fritz Kaegi, the office made a significant leap forward in the technological modernization of the third largest assessment jurisdiction in the nation.  To date, the office has processed approximately 125,000 digital appeal applications and approximately 130,000 exemption applications. The implementation of these online tools is part of a larger project to enhance the technology used by the Assessor’s Office, which will streamline administrative processes for staff and make the property tax system more accessible for taxpayers. The digital innovation efforts of the office were submitted for consideration under a program titled “File Smarter, Not Harder: How the Assessor’s Office Went Digital” in the category of Information Technology.