Ever since I installed Windows 286 on an early PC, I’ve been wary of operating system upgrades. True, I could use a mouse on the split screen of my monochrome monitor. But nothing else seemed to work right.

Just last night I crawled under my desk for the upmteenth time to unplug the power cable from my Matrox Dual Head Digital and reconnect it seconds later. Why? Because when I upgraded one of my Macs to El Capitan — known in the vernacular as El Crapitan — it didn’t quite work right with the Matrox. About every fourth time I re-awake the machine from sleep mode the monitors fail to come back unless I reboot the Matrox splitter. This is after I also updated the Matrox firmware with a download the company promises is El Capitan-compatible.

The Mac, several years old, could barely run El Capitan, officially OS-10 version 11, until I doubled its memory. That took two tries with two brands, because not every memory SIMM is created equal, regardless of how well they snap into the slots. Even so, the machine takes longer to boot, and applications take longer to load and settle themselves into memory. I see much more of Apple’s beach ball, the Infinite Loop’s latter-day successor to the tiny wristwatch.

And we want cars from Silicon Valley?

I sympathize with Army officials. They’re dealing with a major drawdown in the size of the force, recruiting challenges in a nation of chubby young people addicted to Pokémon Go, and the prospect of having thousands of soldiers in Afghanistan ’til the cows come home. Most fearsome, the Army is trying to upgrade more than a million PCs and other devices to Windows 10. And do it by the Defense Department’s 2017 deadline.

Army officials worry that too many of their existing application systems of record are incompatible with Windows 10. And yet upgrade they must because of DoD policy. From a security and support standpoint, the upgrade makes sense. From an interoperability standpoint it presents significant challenges. If the interfaces between the servers supporting mission systems and the PCs with which users access them get rewritten, it’s hard to predict how that would affect the applications themselves.

So the Army is approaching the migration somewhat the way it might approach Fallujah or Normandy — all out. There’s a general officer steering committee. There’s a synchronized strategy for the back-end infrastructure in Europe and Asia. What the Army won’t be fielding is a lot of bravado. The officer in charge told our Scott Maucione, he doesn’t think the Army will quite make the DoD deadline.

Enemy armies typically understand a superior force’s… well, superiority and give in. But not so a recalcitrant error, or the two-star exec’s printer driver.

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