Cook County’s much-anticipated digital property tax portal — a $47 million overhaul of the county’s legacy billing infrastructure — entered its twelfth month of what officials are calling a “controlled rollout phase,” after a software upgrade in late 2025 delayed property tax bills for tens of thousands of residents and left the county’s IT department in a state described by one insider as “professionally humbling.”

“The system is performing within expected parameters,” said Cook County Assessor communications director Brendan Kolb at a press briefing Tuesday, before declining to specify what those parameters were, who set them, or whether “expected” referred to the county’s expectations or those of the contractor. He then thanked everyone for their patience and left through a side door.

The portal, developed by a firm called SynTrack Civic Solutions (tagline: “Government, But Make It Digital”), was originally contracted in 2019 with a projected go-live date of Q2 2021. It went live in 2024, crashed in 2025, and is currently described on the county website as “in active deployment,” a phrase SynTrack’s documentation defines as “any state in which the system exists and is connected to the internet.”

At issue is what the county termed a “data migration sequencing event” — a phrase its own IT director, in a moment of apparent candor at a January budget hearing, translated as “we moved the files over and some of them ended up in the wrong place, and now when you log in it sometimes shows you someone else’s property.” The county emphasized that this was a “non-critical anomaly” and that affected users had been notified, except for those whose notification emails also went to the wrong address.

Property owners who received delayed bills have been told they will not face penalties, a reassurance that proved less reassuring when the penalty-waiver form was only accessible through the portal.

“I tried to submit the waiver and it asked me to log in,” said Pilsen homeowner Denise Murillo, 52. “When I logged in, it showed me a property in Barrington that I do not own. I submitted the waiver anyway. I have not heard back.”

SynTrack, for its part, released a statement calling the situation “an opportunity to demonstrate our commitment to iterative civic infrastructure improvement,” and announced it had won a contract with three additional counties in Indiana. The company’s LinkedIn page describes its culture as “fast-moving, solutions-oriented, and committed to transforming how government works.” The page has 14 followers.

County Board President Toni Preckwinkle, who approved the SynTrack contract extension in 2023, said at a Tuesday press conference that she was “monitoring the situation closely” and had “every confidence” in the team, before noting that she personally receives her property tax bill by mail.

The county’s IT director, who asked not to be named, confirmed that the portal upgrade also inadvertently disabled the county’s previous legacy system — a 1998 Oracle database he described as “slow but deeply trustworthy, like a very old dog” — meaning there is currently no fallback option. He said the team was “working around the clock” on a fix and asked that the phrase “around the clock” be understood as “in the metaphorical sense.”

As of press time, the Cook County property tax portal was returning a 503 error for approximately 40% of users, which a spokesperson said was “down significantly” from the 68% error rate recorded in January, and which the county considers “measurable progress.”