Sysadmin blog Microsoft makes a number of truly fantastic technologies and it is legitimately at the cutting edge of a number of hybrid cloud technologies. By the same token, Microsoft is also an asshat, so any attempt to make decisions about it gets complicated and messy in a right hurry.

Unfortunately, as refreshes near, making sense of Microsoft is something I am repeatedly asked to do. Every time I attempt to undertake the task I keep returning to the fact that everything hinges on whether or not you trust it.

If you're already using Microsoft technologies, then chances are you're pretty locked in. Microsoft is an expert at ensuring that moving away from any of its platforms is a high friction event. This means that there needs to be a very good reason to move away from Microsoft, regardless of the scope of the product in question, and the move will be both painful and costly.

For those who purposefully narrow the scope of their consideration to the technologies they are asked to implement, there may very well not be a reason to question Microsoft. As one administrator recently put it to me: "It doesn't affect me...why should I care?"

When I look at Microsoft, however, I see more than whether or not there are problems with the latest version of Active Directory. I notice that it started out with an "unlimited" OneDrive offering and has now cut that to 5GB. I remember Microsoft pulling the plug on its DRM servers, screwing anyone who bought music from them. I don't conveniently forget Windows 8, nor the loss of Small Business Server.

If your employer buys you an MSDN subscription every year it is possible that you simply didn't care about the murder of Technet subscriptions, but it is a point I find worth considering. Similarly, many ardent supporters of Microsoft love the Ribbon Bar. I remember how they forced it on users, no matter how many didn't want it.

Visual Studio, Windows 8, Windows 10, even the Azure portal: big UI changes occur all the time in Microsoft's world. Customers are never given a choice. There is no transition period. There is no A/B testing. Microsoft decides, never admits a mistake, never apologizes and very, very rarely accedes to customer demands.

And all of this is before having a discussion about using Windows Updates to distribute malware. Not just recommended updates. Not just important updates. Not even critical updates. In my personal opinion Microsoft violated a sacred trust by using security updates to distribute adware for Windows 10. I am aware that not everyone cares, but I see this as a critical breach of trust.

Right about here is where a fierce debate can be expected to break out about the "validity" of any of the above issues. You've all seen those debates play out and I don't need to re-enact them here. If you are masochistic, just read the comments section; I'm sure every iteration of every nerd argument about every possible angle will be replayed ad nauseam there.

Corporate hubris

What matters is not whether or not you like the Ribbon Bar. What matters are how Microsoft makes changes to products and services and how Microsoft responds to criticism.

When I look at Microsoft I see corporate hubris. Over and over Microsoft is trying to herd businesses into using its cloud services. It wants subscriptions for everything, and they doesn't seem shy about turning the knobs on pricing and/or feature-busting once enough customers have migrated.

In its brave new world everything you do is streamed to it for analysis and changes can't be delayed much (if at all), leaving users at the mercy of whatever Microsoft's UI designers feel like doing and administrators potentially on the hook for anything from API changes to products made obsolete with completely inadequate notice.

I see a company that does whatever it wants, whenever it wants. If enough customers disagree with Microsoft loudly enough, a response will appear on a VP of somethingorother's blog detailing why Microsoft Knows Best and thus nothing will change.

It will be explained in that blog – and repeatedly at during speeches at various conferences – that everyone who disagrees with Microsoft either doesn't know what they are talking about, doesn't understand, doesn't have the data Microsoft does or (my personal favourite) isn't a real (insert job description) anyway.

I see Microsoft cutting the margins that its partners make, and usurping the customer relationship so that, in the end, the partners are completely driven out of business. I see Microsoft changing its development APIs and platforms regularly, frustrating its developer community so tangibly that tens of billions of dollars ended up pissed down the drain on Windows Mobile and UWP plays that nobody bothered to develop applications for.

So overwhelming was the apathy for UWP, and the associated Windows Store that Microsoft ultimately had to climb down on its app hegemony plans, allowing Win32 and .net apps with weaker security to once more be (almost) first class citizens. Like the other (very, very few) mea culpas Microsoft has made, it only came after it was utterly defeated. Defeats that resulted in alienating many.

What matters?

My personal bias against Microsoft is strong because I morally object to many of its actions. Separating moral disapproval from risk analysis can be hard, but it is critical. Vendors cannot be analysed on technological merit alone, especially in today's "as a service" world.

For service providers, reputation and trust are everything. Or, at least, they have been. Microsoft has convinced me it cares nothing for either concept, so how to categorize the risk of getting in bed with them?

Reading the above, it is fair to say that I don't trust Microsoft much. I recognize the desirability of its technologies, but I am deeply uncomfortable placing my genitalia in a vice it controls. It isn't any one thing that makes me feel this way... it's a whole lot of things, taken together.

My clients are generally pretty sensitive to opex costs. Combining the two concerns, I would recommend to my clients to avoid any Microsoft products that currently have subscription versions or look set to in the near future. I suspect that dials which can be turned to try squeezing money out of those who don't have it will be turned. Inartfully, and deleteriously for both vendor and customer.

It's hard to make purely technological arguments against Microsoft these days, and that's a good thing. They've come a long way in that regard and in doing so they have bettered the whole industry. Despite this advancement in capability, I'm far leerier about Microsoft today than I have ever been.

Once you're locked in, it's spectacularly hard to escape, and those vice grips can be awfully tempting when a company has a bad quarter. How important is your ability to trust a vendor? And what actions give you pause? Answers in the comments, please. ®