Jailbreaking Canada

Reclaiming digital sovereignty and disenshittifying our technology

15/167 © Banksy

The internet sucks.

This was one of the starting tenets of a workshop I participated in on November 26, 27, and 28, 2025 featuring futurists and authors Madeline Ashby and Cory Doctorow. Led by OCAD University faculty, Emma Westecott (Digital Futures) and Suzanna Stein (Super-O Lab), the three-day workshop used futures thinking and playful design methods to encourage participants into Jailbreaking Canada and envisioning equitable and sustainable technological futures for all. Thus, dubbed the Playshop.

As an emerging futurist and foresight analyst and expert in Canadian public policy, I could not resist the invitation to join this event. This post summarizes the themes tat informed the Playshop. It includes a special message for those responsible for the technological hellscape we currently inhabit and a call to action to the common person. This is also part of Hawtorn V. Rabot’s plan to jailbreak the algorithm today.

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“The most dangerous idea is that nothing can change.
- Madeline Ashby

Creative community members, like myself, drew inspiration from Doctorow’s activism for breaking tech monopolies, strengthening global regulation and interoperability, and advancing tech-workers’ rights. These ideas were framed by a lecture from Ashby to set the scene: if there is a lock, that means there is something being hidden, but also that there is a key to the lock. Over the course of these three days, we proposed and prototyped ideas, receiving feedback from Ashby, Doctorow, Stein, and Westecott at key stages to inform the final designs.

Enshittification

Cory Doctorow is the science fiction novelist, journalist, and technology activist responsible for the term, “Enshittification.” I am sure, dear reader, you have come across it by now. It is a term that names a phenomenon. It is the process by which commonly used and popular technologies—online and offline—become shit. The lock-in of users and businesses alike to technologies and platforms that make their lives shittier.

In his lecture, (DIGITAL) ELBOWS UP, Doctorow described enshittification as a process of platform decay that is not driven by consumption choice, rather it makes you, the user, the product for consumption. Your attention, your clicks, your likes. He named Canadian policymakers who succumbed to American interventionist anti-circumvention laws that favour monopolists and oligarchs. Doctorow wanted to send a collective message to Tony Clement, in his role as federal Minister of Industry (2008-2011), and James Moore, in his role of Minister of Canadian Heritage and Official Languages (2008-2013):

Fuck you, man!

Both of these elected officials acted recklessly and with neglect toward Canadians when they pushed unpopular anti-circumvention laws through parliament. These individuals’ decisions have enabled American technology companies to hold our most basic tools and digital devices hostage: computers, smartphones, powered wheelchairs, tractors, even cars and their engines. Doctorow said that we, Canadians, get the rights that foreign companies believe we deserve. We need to seize not just the means of manufacturing, but the means of computation itself, back from techno oligarchs.

Now that tariffs have been imposed by the current POTUS, there is no longer incentive to keep these laws. Canadian companies are largely not beneficiaries of anti-circumvention policies. So why keep them? Retaliatory tariffs are making everything more expensive, so why behave?

Keys open doors. But in a jail, the doors won’t let you out.

Elbows up, Canada. It’s time to break out of this jail.

Jailbreaking Canada Playshop

Jailbreaking Canada Brandmark © JC Zhang

It seems to me that tech policy is fast becoming cultural policy, so it made sense for me to jump into this experience. The ways that we communicate and make-meaning—the ways that we create cohesion and public spheres—have become highly digitalized. Barring any series of solar flares and combined natural disasters, we can only expect digitalization to continue. So it is important to remember that for every digital lock, we can design not only software keys, but also backdoors, stealth entrances, even the occasional Molotov cocktail.

Who remembers LimeWire and peer-to-peer file sharing? Are we still doing that? What about the entire LEGO aftermarket? Do you see where I am going with this?

When I think about what might be jailbroken in Canada, I think about border control, citizenship, identity, and the body itself. I think about illness, life and death. I think about all of the fresh water and remember that not all residents have access to clean drinking water. I wonder about (a potentially ever-growing) list of “Official Minority Languages.” I am inspired by the dualism that defines Canadian culture(s).

After the first day of the Playshop, I was left thinking about how we must co-operate with the systems controlling us, escape is useless. I wondered about all of the ways I hide in plain sight. Quieting and covering myself.

The reason we need to start hacking is because we can no longer get what we need to survive. We can no longer trust digital images, social media stories, and now, good lord help us, LLMs might have advertisements built into conversations (read here, here, and here).

Canada, we cannot stand for this. We live in a world where software demons get to decide how many ventilators stay operational in hospitals and where parts-pairing-pixies decide how many EpiPens the world gets. I assure you, they are manufacturing limitations, deciding who lives and who dies. Billionaires are filling gaps and taking policy loopholes to protect their precious riches. The rest is up to us.

This has to stop. Canada, we can end this. Ask me how!

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