In October 2025, Microsoft will stop issuing updates and security patches for Windows 10. By then, it will be four years since Windows 11 was launched. Many organisations which have diligently kept PCs up to date via Windows automated updates should find the transition straightforward. Others may struggle.

Windows 10 won’t switch off overnight, but without the updates and patches, users of the operating system will be more vulnerable to cyber threats. Microsoft is offering some options for those unable to migrate to the new operating system in time, but these are short-term solutions and sub-optimal.

So, who might struggle?

The truth is that a diverse range of businesses could be in trouble, but it’s too simplistic to start blaming organisations for outdated infrastructure or not having implemented regular updates. IT can be complex and confusing and within organisations, multiple factors affect IT decision-making. Whether it’s familiarity with an existing, functional system, lack of investment capacity, a shortage of technical expertise or even little perceived need to upgrade, many businesses have fallen behind.

This technical debt problem was exacerbated by the pandemic. The quick fixes implemented as businesses rushed to remodel their working practices have remained in place. They aren’t perfect – a long way from it – but for now they function.

The critical question is whether or not they will allow the migration to Windows 11. In the all-too-possible nightmare scenario, outdated PCs, cobbled-together integrations and piecemeal architecture will be inadequate, leaving organisations exposed and unable to benefit from the advanced features of the new operating system.

The Windows 11 deadline brings this potential issue into sharp focus, but tech debt is a widescale problem. It can hold a business back in numerous ways, compromising performance and service whilst pushing up costs. And, of course, it poses a significant risk, not just in terms of cybersecurity, but from potential breakdown and service outages. What’s more, an organisation with a tech debt problem may find it becomes more and more difficult to recruit. People actively choose to work for organisations which use the latest technology because doing so boosts their skills and prospects.

We started by talking about a date that’s not too far into the future – October 2025 – but organisations should always have the future in mind when it comes to their technology. A sound, future-proof IT strategy is essential.

If you’d like to talk to us about that, or how to best manage your tech debt, or even about that October 2025 deadline – you know what to do.