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Microsoft's latest screw-ups suggest bigger problems

A monstrous failure of bug patches and Outlook.com leave you wondering who is running the show.

If Microsoft has screwed up worse than this, I don't recall it. The company had to recall six botched fixes issued on Patch Tuesday and suffered outages for SkyDrive and Outlook.com that ran for multiple days. On top of that, a leaked Windows 8.1 build was greeted with an overall "meh" response and the company is being sued over the Surface debacle.

Like I said in my blog on the suggested divestiture of Xbox and Bing, if Microsoft can manage that many irons in the fire, then let them. But now I have to wonder if they can manage.

Let's get the Surface suit out of the way. That was pretty much a given after Microsoft announced in July it would take a $900 million write-down for the flopped tablets. The next day, Microsoft's stock took its biggest dive in years, plunging more than 11%.

For now, I'll put aside the so-so reaction to the Windows 8.1 build. That leaves the two disasters, Outlook/SkyDrive and Patch Tuesday, two problems that really make me wonder if anyone is home in Redmond.

Patch Tuesday recalls almost never happen. In cases involving tough fixes, Microsoft will skip a monthly cycle and come out with the fix one or more months later. Occasionally, there will be a bad patch, but six? And many are unrelated. One involves Exchange 2013, another covers Windows Kernel, while four others all involve Active Directory Federation Services.

How could Microsoft foul up so badly? Mike Cherry at Directions on Microsoft fears it's due to the new "Blue" strategy, which is not just the code name for Windows 8.1, but a faster overall release cycle for fixes and upgrades. Microsoft, he said, had a really good track record for Windows patches prior to this month's debacle. Windows Update works well and has not crashed in recent memory. So they got that much in place.

But the urgency to push out fixes may be the problem, Cherry theorizes. I have to admit I'm at a loss to explain how they managed to pooch six fixes. That suggests adequate testing was not done and no one there had the sense to hold the fixes.

In the past, Microsoft has let bugs and exploits fester in the wild for a few months while it worked on a fix because it would not issue a fix until it was ready. But since it released the fixes, clearly someone inside thought they were good to go.

This many mistakes really indicates a breakdown somewhere along the lines of management. They've never made a mistake like this on this scale, which would seem to indicate that something significant has changed, so perhaps Cherry is right in saying the problem is with the new release cycle.

Either way, it's a serious embarrassment when one of your online services goes offline for three days and you screw up six software patches. It means something is seriously wrong, something that's likely newly-introduced.

Whatever it is, this kind of issue cannot be repeated, or it will do far more damage than the Surface lawsuit.

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