On September 19, 2007, Justice Belobaba, of the Ontario Superior Court of Justice ruled the Adoption Information Disclosure Act as unconstitutional – it breached section 7 of the Canadian Charter of Rights and Freedoms and thus, the sections of the Act relating to access to birth registration information are invalid.

[12] In November 2007, the Toronto Transit Commission (TTC) announced plans to expand its video surveillance program, which resulted in a formal complaint to Commissioner Cavoukian from Privacy International, a U.K.-based organization, citing concerns that the TTC's proposed expansion was a violation of privacy laws.

In response to this complaint, Cavoukian launched an investigation where she ruled that the TTC's expansion of its video surveillance system did not contravene any applicable privacy laws.

She also encouraged the TTC to conduct a pilot project to test the use of a privacy-enhancing video surveillance technology developed by researchers at the University of Toronto.

[3][15] In 2017, Sidewalk Labs, a subsidiary of Alphabet Inc. (parent company of Google LLC), partnered with Waterfront Toronto to begin developing a smart city area in the 12 acre sector called Quayside.

[16] The project was heralded as a premier example that "would develop a whole new district of Toronto as a working model of a new type of smart city".

[19] The proposed Sidewalk Labs development raised concerns around the breadth and depth of information collected under the project's umbrella.

[17][18] These issues were acknowledged by Waterfront Toronto's board of directors in March 2018: "Privacy, data governance, cyber security and the ethical use of technology are complex questions which need to be addressed in a robust way to ensure that the Sidewalk Toronto initiative progresses in a way that encourages innovation while preserving the public good".

[20] By October 2018, Cavoukian resigned from the Sidewalk Labs citing concerns that the project was not consistent with her widely respected "Privacy by Design" principles.

[23] Cavoukian met with Waterfront Toronto on November 5, 2018, to call for the immediate de-identification of data at the source and to express her willingness to continue working with the organization.

That’s not on.”[21] Cavoukian participated in a panel discussion at the 2019 ITAC Smart Cities Technology Summit in Brampton, Ontario.