The commercial real estate industry has spent the past several years investing heavily in technology that can automate the most labor-intensive parts of property tax management. Platforms that track deadlines across thousands of jurisdictions, flag potential delinquencies before they become penalties, process payments automatically, and surface opportunities to appeal assessments have become increasingly sophisticated. That investment is sensible and the tools are improving. But there is a structural problem sitting underneath all of it. The government systems that process property tax obligations are, in many jurisdictions, profoundly broken, and the attempts to fix them have a persistent and expensive tendency to make things worse before they make them better. The private sector may ultimately be better positioned to solve that problem than the governments responsible for it.
The Cook County, Illinois situation is the most dramatic recent example of how badly a government-led property tax technology modernization can go wrong. Cook County property tax refund delays have been plaguing 83,000 property owners who have been waiting on $186 million since May of last year, an average of $2,250 owed to each taxpayer. The problems trace back to a system upgrade contracted to Tyler Technologies, a Texas-based public sector software provider that has become the dominant vendor in the government property tax technology market. Cook County awarded Tyler two contracts since 2015, together totaling nearly $87 million. The upgrade required integrating three county agencies each running different legacy systems and converting 20 years of data. It produced a cascade of failures that extended well beyond the initial refund delays.
The technical problems also delayed the distribution of property tax bills to residents, which were sent in November instead of July, and prevented the distribution of more than $8 billion in property tax funds to local governments including school districts that rely on the revenue. Chicago Public Schools incurred more than $33 million in costs between mid-August and the end of December as a result of the missing revenue, including interest on loans and pension fund obligations it could not meet on time. Palatine School District 15 projected more than $1 million in interest and lost investment income alone. The treasurer’s office attempted to work around Tyler’s system entirely for some distributions, partnering directly with a bank to get $4 billion out to governments while the technology continued to fail. Eventually, Tyler’s business license with the State of Illinois was revoked in September 2025 after the company failed to file an annual report.
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Cook County is not an isolated case. In Jackson County, Missouri, residents received dramatically inflated property tax assessments after the county contracted with Tyler for a reassessment process. Some homeowners saw assessed values increase by more than 90%, and some by as much as 150%, well above what Missouri law allows without a physical property inspection. The Missouri Attorney General and State Tax Commission both filed lawsuits against Jackson County and Tyler Technologies, and the state ultimately ordered the county to roll back its 2023 assessments. A class action lawsuit filed by property owners whose assessments increased more than 15% was certified by a judge in April and remains ongoing. In that case, county officials contended that Tyler bore responsibility for a process that the state auditor found had violated Missouri law in multiple respects.
The reasons government technology modernization efforts fail so consistently are not specific to one vendor. The systems being replaced are often decades old, built on legacy technology that was never designed to be migrated. The organizations overseeing the migration frequently lack the technical expertise to evaluate vendor claims or recognize when a project is going off the rails before it reaches a crisis. Procurement processes that favor the lowest bid over demonstrated capability push jurisdictions toward vendors that win contracts they are not equipped to execute. Tyler’s response to Cook County illustrates how those dynamics play out. The company blamed the county for not providing the data it needed. The county blamed Tyler for incompetent execution. The board president’s office blamed the treasurer. This legal back and forth reflects a governance structure that was not designed to move quickly or hold anyone clearly accountable.
The deeper problem is that government-led property tax modernization efforts are unlikely to produce reliably better results regardless of which vendor gets the contract. The IRS paused parts of its own modernization plan in March of 2025 to reevaluate priorities, the latest in a decades-long pattern of stalled federal technology investment that mirrors what is happening in state and local property tax systems. Government technology procurement is structurally misaligned with successful technology deployment. The incentives reward winning the contract rather than delivering the outcome. The oversight mechanisms are too slow to catch problems before they compound. And the consequence of acknowledging failure is often worse for the officials involved than continuing to fund a project that isn’t working.
The private sector has already demonstrated what a better path looks like. Platforms that process property tax payments, track jurisdictional deadlines, and manage compliance across large portfolios are doing so reliably and at significant scale by building purpose-built technology on top of government data rather than waiting for government systems to improve. That model, where private-sector platforms abstract away the dysfunction of the underlying government infrastructure and deliver consistent outcomes to real estate companies regardless of which county system is working and which isn’t, is the approach that is actually moving the industry forward. Rather than waiting for government systems to improve, private-sector platforms are building around them.
The private sector also has something that government technology programs consistently lack: competitive pressure to solve problems rather than manage them. A company that cannot get payments processed or refunds delivered loses customers. That pressure produces a different quality of outcome than a government contract that pays regardless of whether the system works. And as AI-powered tools become more capable of navigating inconsistent data formats, working around system outages, and flagging jurisdictional anomalies before they become problems, the private sector’s ability to compensate for government infrastructure failures will only grow.
The real estate industry’s most productive path forward is to accelerate investment in private-sector platforms that can absorb as much of the property tax process as possible, and to advocate for the data access and interoperability standards that would allow those platforms to function more effectively across more jurisdictions. The Cook County situation is a demonstration of what happens when an industry depends on government infrastructure that cannot keep pace with what the market needs. The private sector already knows how to build what the property tax system requires. The path forward is not to wait for the government systems to catch up. It is to build around them well enough that their dysfunction stops being the real estate industry’s problem to absorb.