“The day the music died” – Don McLean, in his epic song, American Pie.

I’ve been watching with great interest the efforts of Microsoft to migrate its enterprise customers from perpetual licenses with software assurance to subscriptions.  When we read recently that Terry Myerson was leaving Microsoft and his team was distributed to the four winds, we knew big changes were afoot, but I learned that Microsoft had already sent some signals to the IT community which I had somehow overlooked.  Mind you – I work hard to keep up at technology.  I listen to podcasts like Windows Weekly and This Week in Tech, I read lots and lots of blogs, attend a lot of briefings, and do a lot of tech social media – but somehow I missed something big coming up in 2020 and another event in 2025 which Microsoft signaled in February 2018.

I was preparing to speak at a state CPA technology conference a couple of weeks ago, and noted again that the following end of support dates were pretty close with each other:

• Windows 7, SP1 – End of Extended Support – January 14. 2020
• Office 2010 SP2 – End of Extended Support – October 13, 2020
• Microsoft has also published a blog post here reporting that they will no longer support Windows 8.1 users who also use Office 365 ProPlus (the ENTERPRISE version of Office, on an Office 365 subscription) after January 14, 2020.

Hmmm.  That’s interesting.  Three big ends of support in a relatively small period of time – and the discontinuance of an ENTERPRISE Office 365 SKU on Windows 8.1, less than a year from the end of support for Office 2010 SP2.

I then saw that on October 14, 2025, Microsoft ends support for the following applications:

• Windows 10, 2015 LTSC – End of Extended Support – October 14, 2025
• Office 2016 – End of Extended Support – October 14, 2025
• Office 2019 – End of Support (based on expected 10/2018 release date) – October 14, 2025

They say change comes in threes, so I was intrigued – what were the big things changing in 2020 and 2025?  So, I took to Twitter and asked two leading Microsoft journalists (Mary Jo Foley of ZDNet and Paul Thurrott of Thurrott.com) to tell me what they thought was going to happen:

Paul came back with a quick quip which made me smile:

Mary Jo, however, being the more enterprise-sympathetic of the two, came back with a post she wrote in February of this year about a February Microsoft announcement I had not read as closely as I should have related to the 2020 date – and as usual, when St. Mary Jo speaks, thou shalt listen, and you ignore her at your peril.

I reread her February 2018 article and the related Microsoft blog post.  As expected, the post says that Office 365 ProPlus will no longer be supported on Windows 7 (due to its EOL the same day) and Windows 8.1 as of that date (even though Windows 8.1 support doesn’t end until 2023).  The post also says that you’ll have to be on one of the last two semi-annual channel releases for Windows 10 at that time (e.g. what we used to call “current branch for business”).

But here’s something I missed – you can’t use Office 365 ProPlus on the long-term servicing channel version of Windows 10 Enterprise – the one used by almost every enterprise who implements Windows 10.  So if you took the bait and bought Office 365 ProPlus because it was less expensive than the software assurance alone for previously owned volume licenses of Office, you can’t go home again.  Really.  

Microsoft customers who bought Office 365 ProPlus (the version of Office included in Office 365 enterprise, government, and education SKUs like Office 365 E3 and E5) will be unable to stay on the Long Term Support Channel (LTSC) versions of Windows 10 and use Office 365 ProPlus.  They will have to instead use the semi-annual channel update (formerly known as “current branch for business”) of Windows 10 instead of the LTSC channel.  This has the potential to create many new headaches for Enterprise customers with backward compatibility of legacy applications, as it’s going to force you to update Windows twice a year – so instead of zero Windows feature updates a year under LTSC, you’re going to get two a year – two more opportunities for Windows, drivers, and your apps to find fault with each other’s new bits and decide to not work together.

Big Changes Come in Threes – October 14, 2025 – The Triple Witching Day

Let’s back up and do some finance background here – for those not familiar with the term, a “triple witching hour” is a quarterly time of big volatility in the stock market due to the simultaneous expiration of stock market index futures, stock market index options, and stock options.  (For those who want to know when the actual Triple Witching hour occurs, it’s the last hour of trading – 3-4P ET – on the third Fridays in March, June, September, and December.)  As you can see in the previous part of this post, we’re going to have big changes in 2020 – and possibly bigger changes in October 2025.  I, therefore, declare that henceforth, I will refer to October 14, 2025 as “the Triple Witching Day”.

Given the possible end of perpetual licensing and IT as we know it, let’s go back and look at what’s going to happen on that day, the end of  what I will now call:

Microsoft’s Mayan Calendar of Support Apocalypses:

Microsoft ends support on 10/14/2025 for the following applications:

• Windows 10, 2015 LTSC – End of Extended Support
• Office 2016 – End of Extended Support
• Office 2019 – End of Extended Support (based on expected 10/2018 release date)

So the first version of Windows 10 LTSC (the 2015 version), the one which was likely adopted by many enterprises, is going to end that day.  Office 2016 ends that day – OK, no big deal yet… but this one – Office 2019 ALSO ends that day.  So may be no option but Office 365/Microsoft 365 at that point. 

Let that sink in for a minute.

There may be no option but Office 365 or Microsoft 365 at that point.

What’s really going to happen then?  I have no idea – but it could be–(with apologies to Don McLean) – “The day the (Microsoft perpetual) license dies?”  Mind you – this is not something which has been overtly signaled by Microsoft – it’s all based on inference, speculation, and conjecture (and Paul’s wise crack, which one wonders if he was congratulating himself on being a smart aleck at the same time he was sharing a possible reason for the convergence of those dates).  Either way, it certainly makes for an interesting story, doesn’t it?  And – it makes you think about how long you really have until you’re forced into all subscription, all the time.  Maybe not as long as you think.

Nobody but Microsoft CEO Satya Nadella and maybe a few of his closest apostles know at this point, but I know a company whose SEC filings, press releases, and blog posts I’m going to read with a fine toothed comb for the next few years – because ending perpetual licenses is a very big change which could (and should) influence long-term IT strategy today.  As the details emerge, it should be an interesting few years as we see how hard Microsoft and the other software vendors are going to push hard to move us all to subscriptions running on the cloud – voluntarily – or perhaps involuntarily.

Note: Microsoft PR/WagEd people – would love for you to set the record straight and help me correct any errors I’ve made in this post.  If you would like to make any statements, I’m @BFTCPA, my office number is pretty easy to find online, and I’m in the office from 9-6 ET every day this week.   I’m sure that the two tech journalists I admire most –  @MaryJoFoley and @Thurrott – would also welcome a statement on this.  Help us out here – and please – stamp out any ignorance I have with respect to your future plans – because a lot of people in businesses who use Microsoft Windows, Office, and Windows Server are going to spend a lot of money in the next few years, and it would help them make better investment decisions if they knew more definitively how quickly you’re going to force the laggards to move to the subscriptions and the cloud.