With Microsoft pushing cloud services over on-premises servers, mobile computing devices over traditional PCs, and BYOD over granular management, as well as ending keying programs aimed at helping you advance your career, it's a tough time to be an IT pro. In fact, if my email is any indication, IT pros are more put upon now than ever. Only this time, it's Microsoft and not the user base doing the pushing.

If you've been fully immersed in Microsoft's ecosystem for as long as I have, this is a strange state of affairs. Back in the 1990s, the firm was trying to establish its credibility in business, and a string of software releases that includes LAN Manager, Windows NT, and Exchange catapulted Microsoft first in so-called workgroup computing circles and then upmarket into enterprise data centers. Today, Microsoft is entrenched—like a tick—in business. So why is it ostensibly turning its back on us?

I caught wind of these changing times two years ago at TechEd, when Windows IT Pro hosted a pre-conference session aimed at communicating Microsoft's plans for cloud computing. We divided the audience into two groups, and while some enjoyed an afternoon of celebration with developers, I ended up in the IT pro group. It was like a funeral.

"So you're telling me," one dazed IT pro asked me during the session, "that my final act as an Exchange admin will be to migrate my company's servers to Office 365?"

This question has stuck with me since then, and indeed has sort of haunted me. I explained at the time, as did others, that as part of the technology revolution, IT was an ever-changing field. And that on-the-job training—including for those topics that might lead to a related job change—was a central tenet. But I also understand that migrating from Exchange 2003 to Exchange 2007, while potentially painful at the time, is a far cry from migrating from Exchange 2010 to an externally-hosted cloud service. It's hard to ask someone to make the right decision for their company when doing the right thing could result in them losing their job.

Ironically, this same Catch-22 is part of the reason Steve Ballmer and Microsoft's board of directors have been unable to make the right strategic moves for the erstwhile software giant, which is so busy trying to recast itself as a devices and services company that it's lost sight of how it got here in the first place. Microsoft does offer customers a unique opportunity to bridge the gap between the past and the present by providing so-called hybrid solutions in which those customers can maintain some on-premises resources and combine, or federate, them with cloud-hosted services. But the end game is clear enough: Microsoft intends to move from software to services, and it intends to take its customers with it.

Many customers are balking at this so-called journey. Some have regulatory needs that may or may never be satisfied by cloud services. Some simply don't like the idea of relying on external hosters and services providers. Some, yes, are simply old-fashioned. But as Microsoft moves inexorably to the cloud, many see choice disappearing. It's like one of those "rail"-style video games. Yes, you can go left or right in some places, but you're always going to get from A to B whether you want to or not.

And then this year happened.

First, Microsoft unleashed its most impressive and feature-complete Office 365 version yet, making a very credible case for the move to cloud computing. And then the company proceeded to reward early adopters—those who came on board before the January refresh—by keeping them on the old version and not updating them. Some customers are still waiting for that upgrade, a situation that flies in the very face of a primary benefit of cloud computing. Microsoft, if we wanted to be stuck on the previous version, we would have installed Exchange 2010 on-premises.

Then, Microsoft committed what I consider to be the cardinal sin of the year when it announced the cancellation of its TechNet subscriptions. These wonderful and inexpensive subscriptions allowed IT pros—and, heck, budding IT pros—to use the firm's business products on their own hardware, creating their own test environments, learning new products and technologies, and keeping up to date on new software versions, even if their employer was stuck on an older version. But they also apparently allowed these same customers to basically steal software, since the liberal licensing terms meant they could easily do things like install Windows on multiple computers in their home. Piracy bad. TechNet dead.

(A petition to get Microsoft to change this decision has garnered almost 11,000 signatures at this writing.)

More recently, Microsoft has cancelled some of its certifications, raising questions about how far those cuts might go in the near future. Citing changes in the marketplace, the firm will no longer offer Masters and Architect level training and will be retiring the Masters level certification exams at the end of October. According to Microsoft's Senior Director of Microsoft Learning Tim Sneath, the Masters program certified just a couple of hundred people each year. But I feel like I've heard from most of them. They're not happy.

So, is this all sour grapes? Isn't Microsoft justified in moving with the market to cloud computing (services) and devices?

Sort of. But Microsoft's continued focus on product lines that do nothing but hemorrhage revenues—not just devices (Xbox, Surface) and services (Bing, online advertising) but much of its consumer-oriented portfolio—makes its seeming antagonism to business customers all the stranger. In his exit interview with Mary Jo Foley, outgoing Microsoft CEO Steve Ballmer spoke eloquently of the need for Microsoft to make both consumer and business products. But I see precious real-world advantages to this, and in fact can cite more examples where supposedly similar products—such as Outlook.com and Exchange Online/Office 365—in fact bear startlingly little technical overlap. And as Google and Apple's focus on consumers has led them to great success, maybe Microsoft needs to focus solely on those customers that historically, as now, have been the company's primary source of revenues: businesses.

Maybe Microsoft should treat its consumer products like incubation projects: Build them out, establish the brand, and then spin them off. Certainly, I can make more of a case for a purely business-focused Microsoft than anything else.

But then that's not my place, and any future direction is of course for Microsoft's next CEO to decide. For now, IT pros are understandably—not necessarily justifiably, but certainly understandably—concerned with the events of late. This is a situation Microsoft needs to address.