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Most of the world’s business applications depend upon a certain server whose manufacturer can no longer afford to produce it indefinitely and whose users just don’t find exciting any more.

Rather than just raise a giant white flag, Microsoft made genuine efforts over the past two weeks of conferences to signal a change in course.

That’s good news for users who never embraced Windows 8. But it’s scary for system administrators, whose skills could soon become largely irrelevant, as well as for developers, who may soon be faced with having to move decades of business logic from obsolete reporting systems into the cloud.

A Lot to Discuss

So suffice it to say, there were many emerging issues at Microsoft's Ignite conference in Chicago last week, beyond our previously identified Three Keys to the Conference. Let’s revisit those first:

Can the new Windows popularize cloud applications?

Three years ago, when I declared the Windows Store No. 1 on my list of Top 10 Windows 8 features, it was not because I thought Store would necessarily be anything marvelous. As I described at the time, the success or failure of the operating system would depend on whether users embraced Store as a platform ecosystem on the order of iTunes or the Google Play Store.

Windows 8 failed spectacularly. Although I'm on record as having said the Start Screen was soundly rejected by users, there’s a chance Windows 8 and 8.1 could have enjoyed even mediocre success had there been any reason for users to visit the Windows Store.

Today, Microsoft knows what it means to strike out. In fact, Windows Server lead architect Jeffrey Snover, from time to time, demonstrated the act with gestures.

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At Ignite this year, the company’s engineers made it clear they understand what is required to make Windows 10 a success: a system that is truly cloud-based and delivers applications to their users — along with their documents and preferences — on whatever Windows 10 device they happen to use.

It's a much taller order now than for Windows 8, and users this time are ready to reject Windows 10 even if it stays free for the rest of their lives. But if Windows 10 remains successful after its first year of deployment, it will be because the Windows 10 Store delivered users the functionality they expect.

Will Windows Server “embrace and extend” Docker or will Docker “slice and dice” Windows Server?

In another time and place, Microsoft’s notion of “embrace and extend” was to reproduce someone else’s idea and broadcast it in an unavoidable way. Today, the company can no longer afford that luxury. It may still be a monopoly player, according to the European Union, but in a market that modern technology is close to rendering meaningless.

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The embrace is real. Though admins proficient in Docker and its related technologies like Kubernetes and Mesos were few in number last week, you could spot them easily by the logos on their T-shirts and their PCs. They felt the warmth personally, and a few may have been a little stunned by it.

Microsoft’s senior officials made clear to me this week that adopting a containerized architecture, with servers running thousands of little operating systems instead of one big one was a physical and financial necessity for it to deploy its own profitable services on Azure.

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The Azure and Windows Server teams worked together on this, meaning they were in the same room and even eating the same meals (though presumably off of their own plates).

Azure CTO Mark Russinovich (right) dispelled any notion that the old silo walls may still be in existence by using a term for a certain bovine business.

Microsoft officials stated publicly that they were embarking on a road leading them to someplace unfamiliar, a world whose dynamics five years from now they’re not yet capable of imagining. Whether we still call it “Windows Server” at that time, is indeterminate.

And that’s a huge problem for the certified professionals attending last week, who read into those concessions that their skill sets were being outmoded.

Just what is Microsoft’s communications plan this year?

The enterprise communications company that goes by the name of Microsoft still resembles the corporation of ten years ago, in a way that the operating systems division has ceased to.

Continuous deployment and cloud-based integration is not the order of business for the communications side. While we expected to see more and more Skype integration into Windows 10 with each new test build, the fact is, we’ve seen less. And while the Skype for Business logo appears in mockups of the future Office 16, that’s all it is for now: a logo.

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The extension of the Skype brand into the business side, formerly the territory of Lync, was supposed to have been an integration of Skype’s classic P2P communications protocols into the Microsoft stream.

But when I asked officials at Ignite to explain what benefits that brought to Lync, they couldn’t actually describe them.

When given the opportunity to compare Skype for Business against WebEx or GoToMeeting, they were the masters of metaphors and, on occasion, of smackdowns. But when I asked how Skype intended to compete against WebEx’s and Spark’s notions of meeting rooms and conversation streams, I heard an old familiar line: “We’re listening to our customers.”

That’s not exactly what continuous deployment means: giving customers the keys to the kingdom, and expecting them to architect the castle.

In a completely different business unit, however, Microsoft is betting the castle on building an events architecture around Office and SharePoint. Office Graph will give Delve users real time data on co-workers’ collaborative activities.

Trust the Bank

The depths of those activities scared some analysts I spoke with at Ignite, who believed its granularity could expose Microsoft to legal and even governmental challenges, especially in the E.U. That Microsoft would even think it could get away with this much depth, one analyst told me, reminded him that this was still the Microsoft of old — the arrogant, boisterous men’s club that thought its own rules superseded laws.

When I shared that point of view with Broadcom’s chief SharePoint programmer Larry Somers, the bovine business word crept back into the discussion.

Real corporations aren’t afraid of the cloud, Somers told me in no uncertain terms, reminding me that Broadcom technology pervades a majority of the world’s communications devices. They’re not afraid of entrusting their business data to Microsoft, for the plain and simple reason that Microsoft’s engineers are typically more trustworthy than their own.

It’s the difference, said Somers, between storing your money under the mattress and storing it in a bank. Once businesses come to their senses and perceive that data is money, he said, they’ll trust the bank and they’ll rest easier.

He also implied that if analysts would actually talk to some real corporations, they might learn this too.

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It was, as Russinovich put it, “the best Ignite ever.” Quite logical, since it was the first one ever.

But it was a very different conference, in spirit and execution, than anything produced by CEO Satya Nadella’s predecessors. The conversations were two-way, if not three-way, and Microsoft’s people did some actual listening.

I would say we’d know whether they heard what they listened to when we come back in a year’s time.

But this is the era of continuous deployment. We’ll know whether they really listened in about two months.

Creative Commons Creative Commons Attribution 2.0 Generic License  Title image by Sgt. Pepper57.