Windsor council backs extended app parking time, stops short of full cashless system

From the future of street parking to a debate surrounding a crown jewel of Windsor's past, CTV Windsor’s Sanjay Maru has more from council.

Windsor city councillors have voted in favour of allowing users of the city’s parking app to extend their stay up to four hours — but stopped short of endorsing a full transition to a cashless system.

Until now, app users could only pay for up to two hours of parking at a time.

A motion introduced by Ward 3 Coun. Renaldo Agostino during the May 12 meeting of Windsor city council doubles the allowable parking time, in hopes that it will help steer more people toward digital payments without alienating those who still rely on cash.

“This is one of those very complicated issues that isn’t really so complicated,” Agostino said. “We know this is coming, whether it’s today, tomorrow or next year — but we don’t have to take the giant leap just yet.”

Council’s decision comes amid extensive debate over the city’s plan to modernize its aging parking infrastructure.

Administration’s preferred approach — outlined in a report authored by parking coordinator Bill Kralovensky — called for the immediate removal of cash payment options at all metered street parking spots.

That shift would have cost $144,745.04 and involved covering coin slots and installing mobile licence plate recognition (LPR) scanners.

While the majority of council agreed modernization is inevitable, several expressed concern that the city’s population — particularly older adults — isn’t ready for an abrupt shift.

“It might be a year, two years, five years. But at this point in time, I just don’t think we’re ready,” said Ward 1 Coun. Fred Francis.

Kralovensky said more than 52 per cent of street parking transactions were made through the Passport app by the end of last year. Since the start of 2025, app usage has dropped to 39 per cent.

The report also revealed that $1.3 million in parking fines remain unpaid in Windsor.

Ward 4 Coun. Mark McKenzie called that figure “a lot of money” and proposed a friendly amendment to ask the province for help enforcing outstanding tickets. The amendment was accepted unanimously.

Kralovensky noted the city is working with communications staff and senior centers such as Life After 50 to improve app literacy.

“It’s a choice,” said resident Mike Mastromattei, who phoned in as a delegate. “If certain people choose not to use an app, they shouldn’t be relegated to specific areas of the city.”

Mastromattei argued the shift away from “legal tender” infringes on personal autonomy and questioned the security of digital payments — concerns Kralovensky attempted to assuage by citing strict PCI compliance requirements and local data storage protocols.

Despite administration’s recommendation to move forward with an app-only system, council opted for a more gradual approach.

The motion passed allows users to extend parking time up to four hours via the app — a move supporters around the council table hope will organically boost adoption rates without alienating less tech-savvy residents.

Councillors also expressed interest in revisiting broader modernization options at a later date.

“We might have been able to take an even more bold step today,” said Ward 9 Coun. Kieran McKenzie. “But I’ll look forward to where this goes moving forward.”