There’s a big announcement and it’s time to pay attention…

If you have read any of the Microsoft marketing material regarding migrating to Windows 10 in the past three years, you know that the software giant heard past complaints and frustrations about past transitioning pains loud and clear.

Just look at Microsoft’s own migration story of migrating 94,000 employees to Windows 10 or the Forrester Total Economic Impact Report. The marketing message is heavily focused on touting the speed and ease of migration and management. But how much of this can you actually believe? To answer that question, let’s take a minute and take a closer look at Microsoft’s “Ease of Deployment” marketing message before diving deeper into reality.

Windows 10 Marketing Message

Microsoft’s Ease of Deployment Marketing Message

One of the best marketing assets that really drives home the message of easy and fast deployment is the Microsoft-commissioned Forrester study ‘Total Economic Impact™ (TEI) study of Windows 10′. In the summary, you will read:

“The updated study shows the three-year net present value of benefits per user increased from $403 to $515 and the Return on Investment grew from 188% to 233%, with a payback period of 13 to 14 months.

This updated study helps provide further evidence that Windows 10 can drive significant cost savings, security and productivity benefits for enterprise customers.

Enterprises that leverage the new tools in Windows 10 to deploy the updated operating system (OS) more quickly and easily than with past efforts have experienced improved boot times, application access, security, and mobility which has helped IT and users increase their productivity and complete their work more effectively.”


(Image Credit: Forrester/Microsoft)

Microsoft continues to tout the ease of deployment, but how much of this message is smoke and mirrors and how much is reality? It’s true that many existing desktop applications are fully compatible with the new OS — meaning applications will work effectively without any changes.

Enterprise Adoption Lags Behind

If you look to the adoption numbers, you will find that the new operating system was the fastest adopted OS in Microsoft’s long history (mainly due to the free conversion program right after the initial release), but businesses have been slower to make the switch.

Now that two years have passed since the initial release, enterprises are starting to embrace the new platform — mainly driven by advanced security improvements (49%) and better cloud integration (38%). In fact, according to Gartner, “85 percent of enterprises will have started Windows 10 deployments by the end of 2017.”

This isn’t surprising — it is expected for enterprises to delay the adoption of a new OS for at least 18-24 months after its initial release. The updated platform offers significant benefits in terms of security and ease of use, but there are still some hurdles to overcome throughout the course of a transformation project.

You could blame the impact on purchasing cycles, drains on your IT budget, and the pure disruption of a project of this scale, as undertaking this platform shift is a significant investment for your organization. However, in my opinion, enterprises waited longer to understand how Windows-as-a-Service would play out.

Enterprise IT Managers needed to first understand how they could manage such frequent upgrade cycles, whether they should manage upgrade rollouts as part of their BAU organization or rather within a dedicated Windows 10 project team, how they would handle application certification testing, and so on.

Historical Migration Pain Points

The shift from XP to Windows 7 was a painful one for many IT Project Managers due to the need to retool the back-end infrastructure before migration. In-place upgrades were nearly impossible, with a clean Custom Install being the Microsoft-recommended option.

Even though document access was maintained during this process, older applications were completely unavailable once the new OS was in place. Each system would need to go through the installation process, then reinstallation of applications and finally reconfiguration of all settings.

The wailing and gnashing of teeth was likely audible as project managers attempted to migrate to Windows 7 without losing critical data. Since this happened before the time of easy cloud-based downloads, technicians would often need to visit PCs individually with a stack of CDs in hand to complete the upgrade.

This painful experience caused many organizations to skip Windows 8/8.1 altogether. Microsoft did not want to repeat that experience and therefore focused much of its development efforts on eliminating these pain points.

Microsoft now claims that the migration to Windows 10 will be relatively seamless for most organizations and individuals — so seamless in fact, that you don’t even need to create a dedicated project with skilled resources and extra budget for your migration and subsequent upgrades! This position has gotten already more than one project manager in hot water.

New (Dangerous) Application Testing Philosophy

In addition to the promise of seamless, BAU deployment of the new OS, Microsoft is also telling another compelling story: the extensive application compatibility testing, packaging and re-certification efforts that IT leaders have undertaken as part of a migration in the past will no longer be required.

The software manufacturer is recommending that only critical path applications receive extensive testing, due to the expected higher-level application compatibility:

“With Windows 10, organizations are encouraged to leverage more optimized testing processes, which reflects the higher levels of compatibility that are expected.”

To do so, Microsoft recommends a two-pronged approach:

  • Identify any mission-critical applications and websites that are essential for your operation and focus your testing on this small subset of applications. Microsoft suggests you report any issues using the Windows Feedback tool, so that these issues can be addressed prior to the next Windows release.
  • For any other, less critical applications, Microsoft recommends an “internal flighting” or pilot-based approach. Basically, you deploy the upgrade to a few, selective machines to verify compatibility with hardware and software, and then reactively address any issues before you expand into more advanced deployment rings.

For many experienced packaging managers, engineers, and testers, this narrative may be destined to cause sleepless nights and anxiety attacks. For example, how will you determine which applications are mission-critical?

While Microsoft’s rhetoric sounds positive and achievable, how reasonable is this in a real-life scenario for an enterprise that has a large number of custom-built, non-web-based applications, a variety of different operating system versions (due to BAU rollouts), and a ton of peripherals, application add-ins and other apps that are configured for an aged OS?

Ongoing Windows 10, SCCM & Office 365 Updates

As you probably know, Windows 10 is the last Windows OS that will ever see the light of day as smaller, incremental feature updates are now delivered every six months in addition to monthly security updates.

(For more information about the new Windows 10 Service Model, read our blog post “Windows 10 Branching 101”.)

Given the above-mentioned app compatibility issues and testing complexities, it is easy to see why an organization would want to skip every second update and go on an annual upgrade cycle. However, for larger enterprises, this could mean leaving a large portion of their business users without a supported OS for several months by the second upgrade cycle.

While this is not acceptable to most larger businesses, adding business applications into the mix makes this problem even bigger. Let me illustrate this point in a very simplified scenario.

A lot of financial services companies rely on the money-making business app, Bloomberg, which is a licensed high-risk product that receives updates every month. The updates are linked to the hostname of the machine and have to undergo rigorous testing on a box. They also come packaged with their own version of the .NET Framework and a number of Outlook add-ins.

While Microsoft promised a more synchronized delivery schedule for Windows 10 (2 updates per year), Office 365 (2 updates per year), and SCCM upgrades (3 updates per year), the impact on just this one app is enormous. Now the IT team doesn’t only have to run it through thorough testing for its own monthly updates but also must ensure that the seven updates a year from these three Microsoft products don’t break it as well.

And this is just one business app. On average, an enterprise will touch about 1,500 apps in a desktop transformation project, so you can image how the testing you will have to do will increase exponentially.


After having managed the application estates of major global financial service providers over two past decade, I believe that cutting the number of apps to be tested is a risky path. While you must carefully evaluate the state of your own application landscape and determine which app testing, packaging, and re-certification strategy you will implement, I recommend erring on the side of caution.

Instead of “winging it until something breaks”, we should turn the problem on its head and ask ourselves how we can streamline the resource-hungry processes, eliminate costly bottlenecks and enable even non-technical product owners to self-service their application management needs. And for me, the answer is simple: workflow-based, intelligent automation, like Access CAPTURE provides.

I would love to hear your opinion on this. Do you plan on cutting your testing back or will you ramp it up to meet the needs of a BAU environment? Have you already gone through the process and can share some insights? Please use the comment form below to be part of the discussion. 

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