Microsoft’s decision to extend security updates for Windows 10 offers welcome breathing room for businesses still navigating complex migration paths. The move aligns with the tech giant’s long-standing pattern of accommodating the slower pace of enterprise IT change, giving organizations time to budget, plan and maintain operational continuity.
For many IT teams, this extension helps manage short-term risk and avoid disruption, particularly for those still reliant on existing infrastructure or specialist applications. But while this reprieve buys time, it does also delay the inevitable, potentially compounding the challenge.
As we’ve seen with previous extensions, each delay risks the loss of critical internal knowledge, as the people and vendors who originally managed these systems move on.
Over time, what could have been a straightforward application and data migration becomes a complex, costly rescue mission. The longer businesses wait, the more they risk accumulating technical debt, becoming dependent on expensive external partners and missing out on innovation. As such, organizations must treat the extension as a final window to take action before the real cliff edge arrives.
Here I explore the pros and cons of the recent Windows 10 security update extension and what considerations businesses should be contemplating over the forthcoming months.
Technical Manager at Cloudhouse.
The pros
Let’s start with the obvious. An extension provides extended breathing room and gives organizations more time to plan and execute a migration strategy without immediate pressure. Concurrently, this reduces short-term risk, as continued security updates help mitigate vulnerabilities while businesses remain on Windows 10.
This provides operational continuity and avoids any disruption for businesses still dependent on existing, well-established applications or IT infrastructure.
More broadly, the extension offers budget flexibility. IT departments can spread out migration costs over a longer period, which can help with financial planning, especially in a climate of ongoing budget pressures.
It also provides alignment with past practices, keeping consistent with Microsoft’s historical approach of offering extended support to accommodate slow-moving enterprise migrations.
The cons (and the real risks)
An extension may provide breathing room, but this also creates a false sense of security. More time can encourage complacency, delaying necessary upgrades and strategic planning.
Even more importantly, it can contribute to a loss of internal knowledge. As time passes, key personnel with migration experience may leave, and vendor support may disappear – this makes future transitions harder and riskier.
What’s more, while short-term savings might be gained, there can be increased long-term costs. Maintaining older infrastructure often becomes more expensive than upgrading it, especially when emergency migrations are needed.
Crucially, delays mean companies accumulate technical debt; by not performing migrations, organizations can end up with a backlog of compatibility issues, unsupported applications and outdated hardware.
The combination of losing internal knowledge and maintaining unsupported systems means businesses can become increasingly reliant on expensive external partners to manage complex migrations and increases the chance of vendor lock-in and dependency.
Ultimately, staying on older systems can prevent organizations from leveraging new features, performance improvements, and security enhancements in Windows 11 or alternative operating systems.
A mindset of continuous modernization
The issue with deadlines and extension periods is that they signify an eventual point of completion. In this case, a completed migration project. While they are of course necessary for encouraging organizations to update their Windows applications, they also create the mindset that the process is then a done deal.
But technology quickly evolves and IT infrastructure requires continuous modernization. Having this mentality also avoids companies delaying projects when extensions are provided.
At the same time, existing Windows applications can be critical to operations and not modernizing them before the deadline will bring serious risks. So, how can organizations maintain operational continuity but also modernize over the coming months?
The ‘Rs’ approach – including AWS’ ‘7Rs’ and Gartner’s ‘5Rs’ – presents several strategies. This industry standard process is used by cloud providers and encompasses different ways for companies to carry out migrations for unsupported applications. ‘Retiring’, for instance, involves identifying applications that are no longer useful and can be turned off. Each method has its purpose for various contexts.
But large IT estates can be too unique or complex to use such methods alone. In these cases, external cloud specialists can provide companies with vendor-neutral platforms that allow them to maintain their existing Windows 10 applications but redeploy them onto managed operating systems or cloud environments.
This means applications remain fully operational and secure but can continue to receive security patches, support and software updates. It acts as a smarter alternative to complex migration strategies or the costly redevelopment of applications.
Managing, not delaying, the inevitable
This extension is not a solution, but a grace period. It gives IT teams more time to manage short-term risk. But all an extension really does is delay the same situation repeating itself.
Time and time again we have seen this occurrence take place: a business delays its migration for a year, and then another year, and then – all of a sudden – Microsoft stops the extension of the extension.
The pattern often ends with a scramble when the final deadline hits – by which time the cost, complexity and risk have all increased, internal knowledge to migrate quickly and safely has disappeared, and vendors no longer exist.
So while there are pros to the extension, the cons present very real risks – and they emphasize why businesses need to adopt a mindset of continuous modernization.
The technology and providers are available to help companies maintain their existing Windows 10 applications but move them onto supported operating environments.
In the coming months, rather than delaying the inevitable scramble, IT teams can build ongoing modernization.
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