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The logo of taxi app Uber is shown next to a German taxi sign in Frankfurt. Lawyers for the City of Toronto applied for an injunction with the Ontario Superior Court of Justice on Nov. 18, 2014, requesting that it order Uber to cease all operations in Toronto.KAI PFAFFENBACH/Reuters

On a Monday last month, Luigi Dilorenzo appeared at Uber Toronto's offices, and told the woman at the counter he was interested in becoming an UberX driver. He had submitted an online application three days earlier, and was at the office for training and a background check. Three days later, he was approved.

Unbeknownst to Uber, Mr. Dilorenzo was a private investigator and former Toronto Police officer, hired by the city to pose as an UberX driver and document every detail.

With the city's legal action against the Silicon Valley-based company headed to provincial court – its attempt to shut down the taxi service in Toronto is scheduled for three days of hearings in May – court records obtained by The Globe and Mail reveal that city staff conducted an extensive investigation to prepare their case.

That investigation included hiring Mr. Dilorenzo to pose as an UberX driver, and having Steven Reesor, a former deputy chief with the Toronto Police Service, pose as an Uber rider.

The city concluded that there are "real and urgent" safety problems with Uber, including issues with insurance coverage, driver screening and vehicle inspections.

A spokesman for Uber declined to comment on specific allegations outlined in the reports, but said he's "perplexed" by the city's legal action and that the company stands by its safety record.

"All drivers who partner with Uber for our ride-sharing product, UberX, must undergo a stringent background check and meet certain criteria to gain access to the platform," Xavier Van Chau said in a statement. "Every ride on the UberX platform in Canada is backed by liability insurance covering bodily injury and property damage."

The city first hired Harbour Group Security & Investigations, run by Mr. Reesor, to look into Uber on Oct. 1. Since its launch in Toronto in 2012, Uber has been under intense scrutiny by city officials, who argue that the company – which uses a mobile app to pair taxi riders with drivers – flouts licensing rules. Other cities in the world have also struggled with regulation surrounding the service, and launched similar legal action.

In his report, Mr. Reesor details how, on a Friday, Mr. Dilorenzo submitted his online application to become an UberX driver. The service allows ordinary drivers, as opposed to licensed taxi drivers, to pick up passengers and charge fares in their own cars. That same night, Mr. Dilorenzo received a text message asking him to attend Uber's office for a vehicle inspection.

On Monday, Mr. Dilorenzo reported, he arrived at the office near King and Dufferin streets and was told by a worker "that the Toronto Uber office was signing up about 40 UberX drivers per day."

After overhearing an Uber employee instruct an UberX driver to report an accident he'd had during a fare "to his own insurance," Mr. Dilorenzo said he asked about what kind of insurance he would have as an UberX driver. The company's website states that it provides $5-million in coverage for its drivers.

"She advised him that Uber had insurance that would cover anything his own personal insurance would not," the investigators' report says. Mr. Dilorenzo then asked whether he could have a written copy of the policy, but was told "she had nothing available to hand out."

Mr. Dilorenzo then underwent training, which consisted of a 15-minute video and a 10-question "true/false" quiz, and was told that – pending results of a background check in about 48 hours – his application was complete. At no time, he said, was his car ever inspected.

The city's taxi-licence program requires the completion of a 17-day training course, including a refresher course every four years.

Mr. Reesor raised concerns about Uber's driver-screening process, the documents show. Uber says it conducts five separate background checks on potential drivers – including criminal, traffic, and DUI checks.

"While I am aware from Uber's website that it promotes itself as carrying out a rigorous driver screening process, I have concluded that Uber conducted only a first-level PCRC [Police Criminal Record Check] on PI Dilorenzo …" Mr. Reesor writes in an affidavit. That level of background check, he said, is not intended for people working with vulnerable persons, including disabled people or children.

Mr. Reesor and Mr. Dilorenzo weren't the only ones investigating. Staff in the city's municipal licensing and standards office, led by director Tracey Cook – a former Toronto Police officer – did some digging of their own.

In Ms. Cook's affidavit, she writes that Uber users who agree to its "terms and conditions" are entering into a contract with Uber BV – a private company in the Netherlands. She described this as being of "great concern" because it's an attempt to "distance itself from those it defines as 'transportation providers.'"

When asked about the thoroughness of the probe, city officials said the department treats all investigations similarly.

"The investigation of this issue was undertaken in the same manner we investigate all complaints about a possible contravention of City bylaws," said director of investigations John DeCourcy in a statement.

With a report from Elizabeth Church