Windows 10 is Dead! Migrate to 11 immediately!

Windows 10 is Dead! Migrate to 11 immediately!
Photo by Sunrise King / Unsplash

Shock headlines are good for SEO and making people click, right? Sorry to disappoint, though I do want to explore why every business should consider upgrading to Windows 11 sooner, rather than later.

Windows 11 is now pretty much coming up in every conversation I have with clients, be it in relation to a move to Modern Management via Intune, testing the waters with Windows 365, or just general strategic alignment, and indeed it's pretty difficult for a business to ignore.
Support for Windows 10 has a definitive end date: October 14, 2025, which for reference is this far away >

Windows 10 End of Support Countdown

So I went and compiled a list of reasons I think every business should think about.

Obtaining devices with Windows 10 will become more difficult.

Devices shipped from OEMs and suppliers with Windows 10 installed will become harder to obtain due to OEMs pre-installing Windows 11 by default. While many suppliers can customise the installed OS, this can still cause an impact by limiting the availability of device models, or incurring a cost of requiring the supplier to manually downgrade a device, facing increased lead times, or even then having to be responsible for the “image” the supplier loads.

Application compatibility is almost equal to Windows 10.

While the difficulty encountered by many businesses familiar with previous OS upgrades, such as XP>7 or 7>10, still weighs heavy on the minds of many IT professionals due to incompatibilities with LOB applications, the same cannot be said moving from 10 to 11. Previous OS jumps included major underlying code changes that have not happened between the two latest Operating Systems. Microsoft have heavily invested in application compatibility and provide services such as App Assure and Test Base for Microsoft 365 to try and help resolve issues.

Holding back Windows versions is a legacy mindset.

Due to factors such as application compatibility or projects that have been poorly executed historically, the behaviour and mindset of holding back major (or even minor) OS versions still plagues IT decisionmakers. The knock-on effects of these decisions made each subsequent migration more difficult to accomplish, and more painful for both the business and end-users.

Users are not as frightened of change as you think.

A decent proportion of end-users will have a PC at home and are more than likely going to be running Windows. Assuming a device purchased within the last 3 years, many of them will have been offered the upgrade from 10 to 11, with a proportion of those taking that upgrade. Estimates currently suggest around a 28% adoption of Windows 11 across consumer devices. Users also regularly update their personal mobile phones, and are usually forced to keep them up to date, which itself brings changes and new features. End users are used to change.

Windows 11 is the most secure Windows Operating System to date and is continuing to improve.

Microsoft has learned from its costly mistakes in allowing huge extensions to support on both Windows XP and Windows 7, especially in the context of security. Windows 11 has been built specifically to provide multiple layers of security, right down to the hardware (referred to as "Chip-to-Cloud"), with requirements of a 64-bit processor, TPM 2.0, UEFI and Secure Boot. Availability of enhanced security features to IT administrators, such as Hypervisor-protected code integrity (HVCI), Vulnerable driver block, Credential isolation enabled by default, and Smart App Control and Enhanced Phishing Protection in 22H2 are major security improvements to help combat a constantly moving threat landscape.

Quality Updates are starting to include Features.

Windows 11's November 2022 Cumulative Update included Tabbed File Explorer windows, amongst other things, and this won't be the first or last time something like that happens. Windows is becoming Windows as a Service, a constantly evolving Operating System integrating things either as a result of user feedback and a relatively robust Insider Programme, or due to an ever-changing security threat landscape.

Bigger companies are already embracing Windows 11.

L’Oréal rapidly deploys Windows 11 Enterprise, enhancing productivity and security
Microsoft customer stories. See how Microsoft tools help companies run their business.
Fineksus was one of the first to adopt Windows 11 as part of its continued approach of innovative technology
An expert in financial messaging and anti money-laundering solutions, Fineksus, continues its growth since inception in 2002, through its Microsoft powered software and service offering. The company recently transitioned to Windows 11 as part of its technology pioneering culture.

Experience drives Attitudes

This isn't my first rodeo. Having worked in IT for (gulp) almost 20 years, I've worked through the end of support of both Windows XP and Windows 7. I would also go as far as saying that businesses themselves were at least partially responsible for the difficult, protracted projects and poor end-user experience often seen and reported on. While application compatibility issues, driver problems and data loss concerns means it would be unfair to tar every business with this massive, sweeping statement, the fact remains that the longer-lasting effect caused by those historical projects continues to negatively impact the approaches I hear being taken even now.

"We'll wait until it's stable"
"Our users don't accept change"
"We always delay until the next Service Pack"
"The security team insists on being n-1"

These are all things I've seen and heard people say when it comes to moving to Windows 11, backed by nothing other than historical biases toward OS migrations fueled by personal experience. It's often also accompanied by actual facts that they have been/currently are massively behind or in some cases already out of support for their widely deployed version of Windows 10!
The fact that "Service Packs" haven't been a thing since Windows 7 also dates that particular argument's history very well...

So just change your attitude, right!?

We can all appreciate this one isn't going to be easy. Mindsets are a difficult thing to change, especially ones that may have accompanied stress, sleepless nights and difficult conversations.
But difficult conversations should never be avoided when it comes to the reality of working in our profession in an ever-evolving modern world. Ignorance or even disregard of that reality can have a significant impacts that could range from:
- Your business losing staff due to being unable to learn the key technologies that will support their career.
- A serious cyber attack or data breach resulting in significant damage, both financially and reputationally.

I like having difficult conversations. I enjoy shining a light on failures in processes. Without injecting reality into modern management discussions, everything is always someone else's problem, or a problem for later, or "absolutely fine" because ignorance is bliss. Not everyone is going to like having that happen, and unfortunately those are the people who are going to almost definitely cause whatever project being approached to fail in one way or another.


If you have an open mind, are willing to accept that processes will need to change, that EUC, Infrastructure, Security & Network teams will need to work together rather than in isolation (which form two entirely separate posts I've got in my drafts), that some things are going to be difficult, or that perhaps you need to tackle a different problem than you expected first before being able to get the best outcome...

Attitudes can be changed. Processes can be improved. Goals can be achieved. And everyone across the business will benefit from it.

Wasn't this post about Windows 11?

Oh! Right!

Yes, Windows 11. Do it.

Do it!

But you don't have to do it all at once! Start small!

  • Upgrade all internal IT devices to help build familiarity, especially within support teams.
  • Engage with key department stakeholders, identify appropriate "Champions" who can feed back the user experience and test important Line-of-Business applications.
  • Communicate upcoming changes to users, they'll be far more receptive.
  • Empower users by allowing them an opportunity to "self-serve" the update. Ways to achieve this could be anything from submitting a ticket (manually adding to a security group), joining a public Teams Channel (and driving policy via membership of the M365 Group. Also allows and encourages user feedback!), to using AAD Access Packages (user-driven and entirely automated group membership).
  • Deploy the update broadly by configuring a clearly defined (and communicated) deadline through the Windows Update for Business Deployment Service.

So, in summary:

What are you waiting for? Do it!

After all, time's ticking...

James Robinson

James Robinson

With 20 years of experience, James is a Principal Consultant specialising in Modern Workplace and End User Compute technologies, with a focus on Modern Management and Cloud-Native endpoints.
Brighton(ish), United Kingdom