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What Windows 11 means for IT migration strategies

Two months on from the launch of Windows 11, Mat Clothier, CEO and Founder of Cloudhouse, explains why businesses should start migration planning for Windows 11 and beyond 

Back in 2015, Microsoft mooted the idea that Windows 10 would be the last operating system it needed to launch. Instead of a new edition a few years down the line, it suggested that ongoing updates would be applied periodically as part of a Windows-as-a-service concept that would enable organisations to benefit from the latest patches and security indefinitely. 

Fast forward to October 5, 2021 and Microsoft has launched Windows 11 to supersede Windows 10. With the Windows 10 end-of-life date now set for October 14th 2025, organisations have some decisions to make over the next four years, such as what this means for their IT strategies. 

Don’t leave it too late

Windows 11 Hero-Bloom

Windows 11’s introduction and the eventual obsolescence of Windows 10 is a reminder to organisations of the finite nature of operating systems and server editions. While businesses do have almost four years to plan ahead, external circumstances can move their focus to other areas, such as remote working and front-facing systems, added to which the pace of technological change means they’ll have to consider a variety of factors in their planning for back-end systems. 

Another consideration is that Microsoft is already deprecating features on Windows 10 in preparation for its obsolescence. While the full list may contain features that are relatively minor for most businesses, planning sooner for a move to Windows 11 can help them avoid issues associated with the future removal of a feature that is critical to their operations. 

Of the options on the table, choosing to pay for Microsoft Extended Security Updates (ESUs) to continue running Windows 10 is one that allows critical security updates to be added beyond 2025. But the word ‘critical’ is crucial here in communicating to businesses that ESUs are a last resort option. They do not include new features, customer- requested non-security updates, or design change requests, and only run for a maximum of three years. 

ESUs are also a costly option, as indicated by the price inflation of previous ESUs for Windows Server 2008, which have increased by 75% year-on- year, and Windows Server 2012, with a 75% increase in year one, 100% in year two and 125% in year three. 

The alternative of attempting to avoid ESUs by running an unsupported edition of Windows 10 could prove even more detrimental, with cyber-attackers easily able to exploit weaknesses in an unpatched system. This could lead to a range of unwelcome outcomes, including potential downtime for the business and significant losses in terms of productivity and costs, or a breach of sensitive data and hefty fines from regulatory bodies. 

Managing a migration 

Planning for a migration to Windows 11 as soon as possible will give organisations a secured system that’s resilient to security threats and fully able to support the business. This move, while necessary, brings its own challenges, particularly around application compatibility, that teams will need to take into account. 

One key consideration in the shift from Windows 10 to 11 is the fact that Windows 11 is set to be a 64-bit-only operating system. While this doesn’t mean that 32-bit applications will suddenly be incompatible with the new system, there’s no guarantee that functionality will stay the same or that applications will remain secure without the necessary updates. Any level of incompatibility or downtime could be detrimental for an organisation, particularly in the public sector, where an application may provide a critical service to local people. 

To ensure capability, businesses may choose to rewrite or refactor the troublesome application. However, this process is time-consuming and can involve significant costs and require specialist skills or knowledge, placing particular strain on small to medium- sized businesses, to the extent that businesses can end up replacing or even retiring the application. Where multiple apps need to be shifted, many may do so without an issue, but it only takes one or two problematic cases to slow down the entire process. 

Organisations need supporting solutions that allow them to complete a smooth migration to Windows 11 while ensuring that all their critical applications continue to provide value.  Reaching out to tap into the specialist knowledge and services of a partner that works alongside businesses is a key starting point that can address all of the variables outlined above. 

The answer for applications 

To avoid the fraught process of recoding applications for use on Windows 11, compatibility packaging services provided by a technology partner effectively transplant applications from outdated platforms and place them into the latest Microsoft operating system. Cloudhouse was founded on the principle of fixing these exact problems. 

It works by using install capture and run-time analysis initially to package the application. Redirections are then applied to the application’s file and registry; runtimes are isolated to ensure that only the packaged application uses it; and packages are then deployed with existing management tools and processes. This enables 32-bit applications to be run on 64-bit systems with no compatibility issues.


While the move to Windows 11 will secure operations for a few years, the continuous cycle of technological change means that businesses will need to plan for future developments. To keep tabs on the state of critical applications, organisations can employ a service that allows them to identify what they have in their IT estates and keep tabs on anything that may be non-compliant or out-of-date. 

This allows them to adopt a continuous improvement strategy, where compliance can be achieved automatically thanks to the pursuance of best practice configuration. Organisations can also access historical data, which gives them clarity of how a system has changed over time and where it may be heading in the future. 

Remaining evergreen 

Migration strategies ultimately need to be part of a wider business culture of remaining evergreen in processes and systems and should be a part of any digital transformation strategy. It’s unlikely that Windows 11 will be the last version of the operating system and utilising the right supporting solutions will ensure businesses keep ahead of the curve as technology evolves. Capturing external factors will allow organisations to remain efficient, competitive and profitable and ensure continued value in legacy applications. Migration planning must start now – not just for the move to Windows 11, but beyond. 

About Cloudhouse 

Founded in 2010 and used by hundreds of enterprises globally, London-based Cloudhouse frees enterprises from running unsupported Windows and Citrix platforms by making otherwise incompatible applications run on the newest platforms – whether they run on-premises or in the cloud. Identified as one of the UK’s Fastest Growing Technology Companies by Deloitte, Cloudhouse is also the Preferred Partner globally for the AWS End of Support Migration Programme for Windows Servers (EMP) and a migration partner for Microsoft’s Windows Virtual Desktop. Cloudhouse is relied upon by organisations across all sectors including a number of Government departments, the National Australia Bank, Experian, Royal Mail and Transport for London. 

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