Windows 10 – New rules, new possibilities

Tonight – Microsoft dropped a bomb, again.

In Febuary this year, the day before I was going onto the stage at the Nordic Infrastructure Conference (NIC) in Oslo, Microsoft dropped the first one when the announced the changes to release cadence, support and lifecycle of Windows 10 and Office 365 ProPlus. That evening, I worked hard to update my session on how to manage Windows as a Service to suit the new rules.

Next week, I’ll be presenting the same session again, at the Cloud Infrastruture User Group in London and at the TechUG in Manchester, and again, ill be working hard to once more keep it up to date with new rules.

Just a few hours ago, Jared Spataro (Corporate Vice President for Office and Windows Marketing) published a blogpost that included three announcements: Two great once, which I’ve been keeping my eyes on for a while, that ill explain briefly and get back to in upcoming sessions and blog posts. The third one, to be completely honest, gives me very mixed feelings – a mixture of disappointment, frustration, admiration and hope.

Lets start with the first two:

Desktop Analytics,

Just the last week I delivered a session on Windows Analytics in Glasgow – a session that Ill be delivering in an extended format during Techdays in Sweden in a couple of months. Windows Analytics consist of Upgrade Readiness, Update Compliance and Device Health – and to me, its a vital part of any organizations desktop management infrastructure. It gives you great insight, enables you to make informed decisions and follow up on compliance.

However, its been missing a few pieces – and especially lacked the ability to make the hard choices for us. Now, its being transformed into Desktop Analytics – that promise to enable organizations to drive the adoption and servicing of Windows 10 and Office 365 ProPlus in a completely new way. Using telemetry data and machine learning – it will not just show which apps and drivers that will work on Windows 10, it will even build the most optimal pilot groups for you, based on your unique environment.

This will ensure a great user experience and a efficient, but still high quality, reactive testing. More info on this will be released during Ignite – and ill of course be blogging and speaking about it in a close future.


Desktop App Assure,

Desktop App Assure will soon be yet another service provided by Microsoft FastTrack. This service, that will be offered to customers on Windows 10 Enterprise and Education for free, will ensure that the migration to Windows 10 (or between Windows 10 releases) is a smooth one. Delivering on the promise of app compatibility, customers that struggle with incompatible apps, will get help from FastTrack – again free of charge – to solve the incompatibilities and make the app run on the selected release of Windows 10. This for sure is an welcome addition and something that will put Microsoft closer to their customers – and probably also ensure that the data displayed in Desktop Analytics will be even more accurate. The service will roll out first of all (in preview) in North America October 1st (so just after Ignite) and reach world wide availability in February 2019. Again, more info will be released during Ignite, so ensure to follow me and #KneeDeepinTech on Twitter and also keep an eye out for new podcasts episodes!

Servicing and support flexibility,

Lastly, the biggest and most important announcement – which probably will fill my mind with thoughts for weeks.

I’ve always argued that ANY and EVERY organization out there could adopt Windows as a Service. I’ve never said its easy or without challenges, but no matter the complexity or size I’m still absolutely convinced about it. I’ve had discussions with probably hundreds of organizations over the years since the release of Windows 10. Many of these have been, noisy, to say the least. I’ve read thousands of tweets, posts and blogs around how crazy (and almost evil) Microsoft were when they introduced WaaS. I’ve offered to help, but few have been willing to change. I’ve been proud in supporting the thought and vision of Windows as a Service and the modern desktop.

Just three days ago I had a great meeting with a customer that have changed, and seen all the benefits of it, and they wanted to take the next step. In that meeting, I said that I didn’t believe that Microsoft would change the release cadence or the life cycle of Windows 10 releases. The reason for that? They have success stories, they have (in large part thanks to partners and the community) all the tools necessary to make it work. They have a number of partners & evangelist that been giving the process great thought and ensured a safe, user-friendly and cost efficient servicing model, and they have been defending their vision – in the interest of their customers, IT-security and innovation.

Today, it all changed, again. Ill briefly explain the changes, ill briefly explain the options – and ill definitely get back with more details in upcoming post, talks, webinars and podcasts.

First – there will still be two releases of Windows (and Office ProPlus) every year targeted for Mars and September. However, these two releases will have different length of their lifecycle. All the Mars releases will stay on the current support length of 18 months. The September release will (mind ONLY for Enterprise and Education) have an extended support of 30 months.


Second – all currently released (and supported) versions of Windows 10 (1607, 1703, 1709 and 1803) will get extended support (again ONLY Enterprise and Education) for 30 months in totalt. This will extend the time organizations that already deployed their first version of Windows 10 get to roll out their next feature release of Windows. You can read all about the new end-of-support dates here.

Third – Windows 7 gets new options for extended security updates. If you would like to receive security updates after the official end of support date (January 14 2020) you can pay a per device fee for up to three more years, until January 2023. The price is yet to be announced, but the price per device will increase for each year until January 2023. This offering will be available to any organization with volume licensing for Windows 7 Pro or Enterprise. If you have a Software Assurance agreement, or already own licenses for Windows 10 Enterprise or Education, you’ll get a discounted price.

In addition to this, if you buy the Extended Security Updates (ESU) – you’ll be able to keep on running Office 365 ProPlus on Windows 7 for the duration of your ESU.

Forth – Office 365 ProPlus will be supported on Windows 8.1 until January 2023. Offie 365 ProPlus will be supported on Windows Server 2016 until October 2025.

And Fifth – If you run Office 2016 today and connect to Office Online Service such as Exchange – you’ve received three more years to migrate to the Office 365 ProPlus or Office 2019. The previous statement that Office 2016 would be unable to connect to online services from October 2020 has been change, and 2016 will be able to keep connecting to Exchange online (and other services) until October 2023.

Why is this important and how could this affect my organization?


Basically, Microsoft has listened to their customers and moved back a bit on their vision on moving organizations to a more modern desktop platform. They are still enabling organizations to drive modernization, to stay current, secure and modern. They are now allowing organizations that needed more time to change to do so – to modernize their applications, to change mindset and get current.

Its important, cause it shows that Microsoft listens and are willing to change – and its important because organizations are now being given a choice and a opportunity.

First – you now get more choices when it comes to choosing your Windows Servicing cadence. You can choose to go with only the September release, only the Mars release, both or choose one or both depending on the included features. This is good, and enables organizations that (due to the nature of their work or vertical) had a challenge with the months of release. Ill dig deeper into this topic in upcoming posts.

Second – You get to choose how fast you would like to make your organization more modern. This is something every organization need to consider, choose and plan for. I still recommend that you aim for a fairly quick servicing model, where you enable a more modern workplace and desktop. If you choose to take it a bit slower, ensure that you stay on route and stick to a plan.

What I’m afraid of, is that we in a couple of years time will end up in the exact same discussions again. People do not like change, and (and I honestly hope that I’m wrong here) I believe that some organizations wont change. They may migrate to Windows 10, and yes, they are still forced to upgrade more frequently than before, but there’s not the same need to actually change how they work with IT. There’s not the same need to modernize applications, and they will probably end up with a less secure environment than they would if they kept the, now old, pace of Windows as a Service.

Last words,

There are a huge amount of other opportunities and challenge that needs to be reviewed and discussed following these changes. Ill probably write about a number of them in the following weeks – and we’ll learn plenty more during Ignite.

But – takes this for what it is. This is something many have been asking for, now when they get it, I sure hope they take the opportunity to actually change. To make the most of it – to be thankful for the opportunity and deliver on the promise that many have made: “If we only get a bit more time, we will be able to change”.

So, now you have time. Make the most of it. Get Modern.


As a Solution Architect, Simon inspires customers, partners and colleagues to create the best possible workplace for their users. His main focus is the Windows platform – but todays workplace consists of so much more than that. As an MCT he is passionate about teaching and sharing knowledge. He’s a frequent speaker, blogger and podcaster – as well as a penguin fanatic.

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Posted in Intune, Microsoft, News, Office 365, WaaS Toolbox, Windows 10, Windows as a Service, Windows Insider

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