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A green P parking sign in Toronto.Deborah Baic/The Globe and Mail

The dozens of suit-and-tied bureaucrats arrived first for the announcement, branded an "exciting" step forward. The journalists followed, greeted by a young man with a sign-in sheet and stacks of glossy pamphlets.

Everywhere in the room were printed green signs, the messages punctuated by exclamation marks. And at the back of the room was a huge digital screen, gleaming with promise.

The reason for all the fanfare? The announcement of a parking app that would allow residents in Canada's largest city to finally do what others across the country have done for years: pay for parking with their phones.

The announcement left reporters in the room asking, "What took so long?" And across the city, it sparked debate on another, more persistent question: Why does Toronto so often feel stuck in the past?

By the end of the event, even Mayor John Tory didn't seem all that impressed.

"I don't want to direct this at the parking authority. I think they've done their due diligence, they've done their work over the last period of time to get this right," Mr. Tory said after the city hall announcement on Thursday. "But if you ask the question if the good people of Toronto should be satisfied generally with the pace with which we're modernizing the city and offering services of this kind that have been offered elsewhere, the answer is no."

The mayor is just the latest to voice his frustration at the sluggish pace at which the city has embraced certain technologies.

Getting around the city? Streetcars, which most North American cities stopped using in the mid-20th century. Paying for that streetcar? Tokens you had to buy, until recently, with cash. And applying for a permit or licence with the city? Show up in person, and stand in line.

Thursday's announcement – that Toronto residents will be able to pay for parking at "Green P" lots using a mobile app – is similar to technology already used in cities across Canada, including Montreal, Victoria and Calgary. Calgary has used it since 2007.

In this case, Toronto Parking Authority president Lorne Persiko said the delay was because staff wanted the city's own branded Green P app, and to ensure users don't incur further charges. Other cities, such as Montreal, pass a transaction fee on to users, he said, unlike the free Toronto app.

Some at city hall blamed a culture of conservatism, saying staff are doing the best they can with limited funds.

"Sometimes, the barrier I hit with some of my colleagues is they don't see a need for it," Councillor Paul Ainslie said.

As most offices and organizations move toward Gmail or Cloud-based systems, councillors at city hall are only now moving to Microsoft Outlook, he said. He also pointed to the fact that monthly council and committee agendas – thick documents that often total hundreds of pages – are still printed on paper and hand-delivered to councillors and staff offices, even though the information can be accessed online.

Councillor Gord Perks, meanwhile, pointed to awards the City of Toronto has won for its online meeting monitor system, saying staff could do even better with more funding. "The fundamental problem is there are still some people in the building who think you can get better services for free," he said.

Others such as urbanist Richard Florida, meanwhile, blamed complacency.

"I think what puzzles me is that for a city that was so far ahead on urbanism and urban innovation … how far Toronto has fallen behind," he said. "It sort of happened quietly. It's not like we were all aware of it."

He said a weak mayor system in Canada has also meant municipal politicians are less willing to make the kinds of investments needed to compete with major world cities like New York or Tokyo.

Mr. Tory also pointed to complacency, but laid some of the blame on previous budget cuts.

"I think when you're in an environment where that sort of thing is discouraged, then it doesn't happen. I think as well there just hasn't been the push going on here," he said. "I'm pushing it in every meeting with everyone I meet, saying, 'What are we going to do to make sure we take services to the 21st century?' It'd be a good start to get some of them in the 20th century."

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