In the past few weeks, October 2026 has become known as Black October. This is due to a wave of AI-enabled cybersecurity failures which resulted in many governments, banks and public services taking down their websites to fix security holes before hackers could exploit them. This represents a qualitative turning point for the world’s critical digital infrastructure, specially where AI-assisted hacking is concerned. In reality, however, this is the culmination of a mass of cybersecurity vulnerabilities and risks that had been piling up underneath the surface for the past decade.
As early as 2019, a solid half-decade before the term “AI agent” entered anyone’s head, titan of Wall Street Jamie Dimon had warned that cybersecurity “may very well be the biggest threat to the US financial system”. Two years prior, 16 hospitals in England shut down all non-critical operations due to a ransomware attack. This is not to mention numerous data breaches involving companies such as Equifax, Ticketmaster, Capital One, the CRA, etc. In 2026 alone, both Telus and Loblaws suffered data breaches which leaked the personal information of millions of Canadian residents. All of this is part of an explosive upward trend in both cybersecurity incidents and successful hacks that started well before the current AI boom.
The truth is that companies, especially the big corporations, have enabled this with weak cybersecurity controls. To quote cybersecurity expert Bruce Schneier from 2021, “The market encourages companies to make decisions in their private interest, even if that imperils the broader interests of society…[companies] save money by taking on greater risk and then pass off that risk to the rest of us”. Concretely, this has meant companies cutting cybersecurity teams and outright covering up security incidents such as data breaches (Uber 2016). In a word, Black Octobers are inevitable in an economic system which is governed by the chaos of the profit motive and not by a rational plan.
– Anonymous
