Microsoft released a new update (KB2959977) that fixes the WSUS TLS 1.2 glitch. In addition, Microsoft announced that Windows 8.1 Update and Windows Server 2012 R2 Update do not become mandatory for enterprise customers until after August 12. I think all this shows that Microsoft currently operates with a shaky hand and that hard times are to come for Windows admins.

For the first time in decades, Windows has to compete with other operating systems, which forces Microsoft to shorten release cycles of new features—something new for the software giant. The way in which Microsoft continued after Windows 8 made me notice how uncertain Microsoft’s top management must be.

I don’t remember that there ever was so much discussion and confusion about a Windows update. When I googled the topic, I was surprised how many news sites and blogs covered the WSUS issue. The fact that this Update for Windows 8.1 for Windows Server 2012 R2 is mandatory caused the same kind excitement in the blogosphere.

Windows 8.1 Update and WSUS

Let’s have a look at the technical details first. Windows 8.1 and Windows Server 2012 R2 with the Update (KB2919355) installed are no longer able to connect to WSUS servers if they configured to use SSL and TLS 1.2 is not enabled on the WSUS, which is the default setting. There is a workaround if your WSUS runs on Windows Server 2008 R2 or later, but since Windows Server 2008 doesn’t support TLS 1.2, this doesn’t work for all systems. The new update KB2959977 fixes this issue; now, everyone can install the Update for Windows 8.1 and Windows Server 2012 R2.

The fact that Microsoft had to pull the update for enterprise customers indicates that quite a few Windows shops were affected. And this is the interesting part. Obviously, Microsoft didn’t have enough time to test Windows 8.1 Update.

The result is that many PCs are now disconnected from their update servers just because of a few nice-to-have features. I suppose quite a few admins are now struggling to get the update that fixes this glitch on to those machines that no longer receive updates. I think that cutting off the machine from future updates is the second worst thing a feature update can do. (The worst scenario is that it crashes the machines.)

New update grace period

Many admins of big networks will welcome Microsoft’s decision to extend the “grace period” for installing Windows 8.1 Update to August 12. This seems to have become a general guideline. Feature updates become mandatory after 120 days (rather than 30 days) for enterprise customers. The situation is unchanged for consumer PCs. If a Windows 8.1 PC hasn’t installed the Update by May 13, it will no longer receive additional updates.

The Windows naming confusion

Did you notice something when you read the lines above? It is hard to follow even though the facts are relatively simple. One reason why the story is hard to tell is the unfortunate naming scheme that Microsoft started to use with this “update.” “Windows 8.1 Update”—what a confusing name for an update! Not that “Windows 8.1 Update 1” is much better. At least the “1” makes it clear which update we are talking about amid the myriad other updates. I think the odd naming and the fact that Microsoft changed the name shortly before its release is another hint that shows how hesitant Microsoft is. It also makes it obvious that Microsoft has no clear strategy about future Windows updates. It appears to be all determined by customer feedback. (I will say a word or two about this below.)

In my view, Microsoft should stop this confusing naming of updates and use a new version number for each feature update. The right name for Windows 8.1 Update would have been Windows 8.2. This not only simplifies communication but also demonstrates a firm hand. An “update” is essentially a patch that indicates that something needed to be fixed. This only provides grist to the mills of the naysayers.

That we always have to refer to unhandy KB numbers when we talk about the status of our systems, adds another layer of confusion. Why not use a new version number for Windows on every Patch Tuesday? I very much like how WordPress handles updates. Fixes and security updates change the second decimal place, a change in the first decimal place signifies a feature update, and major releases get a new version number. This type of versioning immensely simplifies troubleshooting because a simple number communicates the status of your system. This also gets the people who are so afraid of changes used to constant modifications and if it is only the version number.

Shorter release cycles

In addition, Microsoft should release new features at even shorter cycles, say every one or two months, but reduce the number of new features with each release. Smaller steps reduce the complexity for developers and admins and therefore minimize the risk of glitches.

New feature updates should be made mandatory after a shorter amount of time. Thirty days are more than enough. The fact that, in the next 120 days, many Windows 8.1 installations will exist with different sets of updates enhances the complexity and increases the risk that new faulty updates will rain on us. Nobody benefits from this.

The “we stick with what we know” faction can be easily calmed down by introducing new Group Policy settings that allow admins to turn off new features. WordPress has its plugin developers for this purpose. This system fosters innovation because the naysayers mostly stay quiet.

The main reason why Windows XP still has a market share of 27 percent is because Microsoft always made such a big deal about a new Windows version. If people would have been familiarized with installing a new Windows version every week, nobody would still use Windows 5.1.

We listen to customers

What worries me even more is this constant talk of “customer feedback” in Microsoft blogs. For me, this always sounds as if Microsoft is dependent on the help of its customers to determine its future strategy. The 120-day grace period is such a customer feedback thing. Windows 8.1 and Windows 8.1 Update are products created by customers. This constant speculation about the revival of the Start Menu expresses how little authority Microsoft has over the design of its products.

The danger of this “we listen to our customers” thing is that those customers who are unhappy with an ever-faster changing IT world are always the loudest, and it appears to me that Microsoft mostly listens to those naysayers.

I am the exact opposite of a Steve Jobs fan. But I think he got at least one thing right. A company that wants to lead doesn’t listen to its customers; it has to know what customers need long before they know it, and it has to have the authority to tell customers what they want. A company that constantly has to fix unsuccessful updates will be unable to innovate fast enough to compete with rivals that continually get stronger.

This “customer-listening approach” is typical for a company that has a sales guru as CEO. Ballmer’s main job was to listen to big customers and then tell the tech teams to create the corresponding products. This strategy failed and made Microsoft always lag behind new trends because the people Ballmer mostly talked to were only managers and not inventors and innovators. My hope still is that Microsoft's new CEO can change this “we listen to our customers” attitude into a “we listen to our Nadella” approach that is worthy of a tech company that is willing to lead with a firm hand.

Hard times for admins and users

What does this mean for the Windows admin? This serious WSUS bug also indicates that Microsoft is not really prepared to offer new features at the current pace. Until Microsoft has reorganized its update strategy, admins who are responsible for deploying updates will have hard times to come. Many organizations will need to introduce update specialists, that’s for sure.

If Microsoft continues to operate with this shaky hand, and releases changes that are taken back a few months later because the naysayers want to stick with what they know, it will not only significantly increase the workload of admins, it will also confuse end users. Imagine what those organizations, which updated early to Windows 8 and educated their users to work without the Start Menu, will experience when it turns out that it all was only a false alarm.

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What’s your take? Do you like Microsoft’s new release cycle strategy? Do you agree that the versioning of Windows updates is confusing?

  1. Stefan Luccio 9 years ago

    This is just another proof that Microsoft is not testing and/or releasing updates too way fast ! How many updates we already had ? Win 8, then Win8.1 and then Win8.1 Update 1 … that’s just unworkable in a coporate environment ! … but anyway thank you for this article 🙂

  2. Larry Fugate 9 years ago

    This is just another piece of evidence for the fact that Microsoft did not intend Windows 8.x for corporate environments. The “Metro” interface, the insitance on keeping it even and they allow users to “go back tio the desktop”, and this current debacle point clearly to a lack of support in the WIndows 8.x area at Microsoft for corporate users. This will contribute more than anything else to the death of the windows desktop.

  3. Stefan, yeah that’s theory. A wrong theory. I think corporate IT has to change fundamentally within the next years. Innovation in IT is faster than ever before and businesses have to adapt. This means that they have to invest more in their IT staff. Those companies who are unable to keep up with the new speed will die. The naysayers would just drag down Microsoft if they continue to listen to them.

    Larry, you are right. The new UI was built for the consumer market. However, the Modern UI will evolve and will eventually replace the conventional desktop UI. Thus, I absolutely agree. The Windows desktop will die.

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