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Tyler Technologies, the company that has spent more than a decade helming the troubled and often-stalled overhaul of Cook County’s property tax technology that has led to repeated delays in homeowners getting their bills, is in line for a two-year extension.

If the county board approves a renewal next month, the Texas-based company will make up to $18 million more. That would bring Tyler’s county taxpayer tab to $56.4 million from 2015 to 2029 for being in charge of a project outgoing Commissioner Sean Morrison described Thursday as “a cluster—-.”

Many commissioners, while frustrated with the company, acknowledged they are essentially stuck. Tyler is among the most dominant government tech services contractors in the country, having acquired many of its competitors in recent years. Few, if any, could step in to replace them, let alone immediately.

“The problem is, for what we need, it’s not like there’s many other options unless we build it ourselves,” Sean Morrison said Thursday.

Commissioner Kevin Morrison, the chair of the county’s Technology and Innovation committee, agreed. “There are no good answers,” he said. “There are no companies that are capable of dealing with a county as large as Cook. And in terms of doing right for our taxpayers, we have to stay this course.”

The proposed extension does not count the millions it has cost to maintain the county’s old mainframe computer systems during the upgrade, the outside consultants to usher the project along, nor Tyler’s separate $48.1 million contract with the Cook County Circuit Court Clerk to maintain records for the judicial system.

The renewal would pay for upkeep of the county’s Integrated Property Tax System for the next few years, plus any enhancements the county clerk, assessor and treasurer’s offices use.

Tyler has defended its work throughout, noting the various county offices proposed evolving requirements and had fragmented data that required significant cleanup. The company has faced prolonged resistance from Cook County Treasurer Maria Pappas in particular.

Asked whether the county was considering putting out another request for proposals for a new contractor, Cook County Board President Toni Preckwinkle said, “The lesson we’re carrying forward is the need for clear, consistent oversight now that the system is in daily use, so we’ll continue with this provider to be sure that we have the support that we need for the software.”

Preckwinkle’s Bureau of Technology has refereed the project, but separately elected offices have been in charge of executing their respective pieces.

Tyler is still on the hook to help fix outstanding problems at the Treasurer’s office involving property tax revenue payouts and distribution reports to local governments across the county, and pay out refunds to taxpayers. As of the start of October, some 2,200 taxpayers still haven’t been sent their second installment property tax bills and more than 75,000 have not received refunds, according to the county’s property tax tracker.

The county expects modules for the annual tax sale and redemptions for overdue bills will be finished by December. There is a “holdback provision” as part of the original contract stipulating Tyler can’t be paid until all the current problems are resolved, Technology Chief Tom Lynch said Thursday.

The contract renewal for “annual software support and maintenance” would cost up to $7.4 million next year and $7.8 million in 2028. It also includes $2.7 million for the first four months of 2029. Preckwinkle procurement chief Raffi Sarrafian said because the extension hadn’t been approved yet, he could not discuss whether the county is paying full price or received any discounts given the strife over the past decade.

The original $30 million contract, awarded after a public request for proposals, allowed for up to nine years of extensions. The county considered firing Tyler roughly four years into the project and commissioned an April 2020 report to explore other options, but “every separately elected official, every single one, decided to move forward with Tyler then,” Preckwinkle noted Thursday.

The county board increased the contract by $8.4 million in the summer of 2022.

Even Pappas, one of the company’s loudest and most blunt critics, was muted when asked about the prospect of the renewal. In an emailed statement, spokesman Mike Puccinelli acknowledged there were “numerous system defects and data conversion errors,” but “incremental progress toward a fully functional system continues.”

Pappas’ office, which mails the bills at the tail end of the property tax process, most recently used artificial intelligence to help clear up some of the refund backlog. Puccinelli said the office would use Tyler’s system to administer the next sale of delinquent property taxes in December “and will continue to use Tyler’s proprietary system to issue all types of property tax refunds even as remaining defects and data conversion errors are identified and resolved.”

Mark Hawkins, rear, of Tyler Technologies, listens as Cook County Chief Information Officer Tom Lynch address a meeting of the Cook County Board's technology committee in Chicago on April 9, 2025. (Terrence Antonio James/baiduhai)
Mark Hawkins, rear, of Tyler Technologies, listens as Cook County Chief Information Officer Tom Lynch address a meeting of the Cook County Board's technology committee in Chicago on April 9, 2025. (Terrence Antonio James/baiduhai)

“We’re close, we’re going to get there, it’s going to get done. But boy, you talk about massively blowing a budget and massively blowing time and delivery, they take the cake,” Sean Morrison told the Tribune Thursday, acknowledging the blame-games and infighting that characterized the latter years of the project were not helpful. Morrison credited the county’s Bureau of Technology for later cleaning up the agreement by tying payments to completed tasks. The county reached its long-awaited goal of getting off of old mainframe computers in July.

The county’s inspector general, echoing Tribune and Injustice Watch reporting last spring, found a “myriad of problems spread across all parties involved … created a ‘perfect storm’ and severely delayed the implementation” of the property tax project. Because of persistent problems, the county held back an estimated $15 million from Tyler over four years, according to the report, which concluded the county should have brought on outside help sooner and that Pappas was “less than fully cooperative” with the project’s implementation.

Those problems mostly stayed behind-the-scenes until the very public delays issuing property tax bills and remitting money to local governments. Many schools, libraries and villages had to borrow, tap reserves, or delay other spending while they waited for those revenues to come through.

The county board separately approved Commissioner Alma Anaya’s proposal to prohibit private companies with county contracts from selling and sharing that information with third parties, and the release of that information for federal immigration enforcement.

“Government works only when people have trust in our institutions. When residents share their personal information to get care, to enroll a child or seek help, they deserve to know that it will be used to serve them, not to target them,” Preckwinkle said, describing the change as a digital extension of the county’s welcoming policies.