[Disclosure: Microsoft is a client of the author.]
Windows is pretty unique in the segment if you think about it. For most everything else we use, the hardware and software come from – and get support from – the same company. For most of our other devices, tools, equipment, etc., a major software update will only come when we buy a new system.
The good part of this is that our PCs are more up to date than our cars, appliances and other integrated products. The bad news is if we don’t want to update, we don’t have to – and a lot of us don’t like the update process and are sometimes back a couple of generations on the OS. (I won’t even mention the folks still using Windows XP, because they’re in their own unique and painful world at the moment.)
Even smartphone software upgrades often require a new phone after one OS version, and only Tesla in the automotive space does major revisions to their operating systems and experience. So, the situation with Windows, at least with personal technology, is unique. However, it’s also somewhat painful, because older versions of the OS tend to be relatively un-secure compared to newer versions, and the upgrade path is best done linearly. Dropping too far back has serious risks.
Now, thanks to Windows 8’s poor reception, Microsoft has left Windows 7 in place for an extended period – but that time runs out in January.
To help users of Windows 7, Microsoft has released a tool called FastTrack. If you’re like a lot of people, you’re probably hoping enough of your peers won’t move and that Microsoft will extend the expiration date of this product. And that’s been a reasonable bet in the past.
But with the number of user-oriented threats multiplying and Windows 7 on a codebase that was never designed to resist the current threat level, the risks are increasingly more substantial – not least of which is the OEMs don’t want to support this old OS, either. Windows 7 is now 10 years old and in the prior decade we got Windows 2000, Windows XP, Windows Vista and Windows 7. Back then, the threats were much lower. And 10 years using the same OS is a long time, by any measurement.
Lucky for Windows 8
I doubt anyone connected with Windows 8 would call it lucky but thanks to it doing so badly, there’s a decent path from Windows 7 to 10. Typically, skipping ahead two versions of a Microsoft OS would be exceedingly painful. Not that the 7-to-10 upgrade path isn’t without pain, mind you.
When it comes to upgrading the OS on PCs, you neither want to move too early nor too late. The reason you typically didn’t want to move early on a new OS was that there were usually a ton of yet-unknown problems and, if you migrated early, it was your folks that discovered them. The good news is Microsoft has significantly slowed – if not eliminated – major upgrades, so this shouldn’t be a recurring problem, barring another policy change.
But the reason you don’t want to migrate too late is hardware and application support. Let’s face it: most of the development staff moves to the new platform within the first two years. And that’s when you want to have completed your move as well. Now, sadly, if you’re on Windows 7 the ease of upgrading has significantly degraded from what it was three years ago. This reduction in support, security and compatibility is why a program like FastTrack is now critical: it helps you avoid the pain that a late move typically generates.
Moving sucks, whether it’ s moving offices, moving homes (I hope I never have to do that again) or moving operating systems. The good news – and I’ve been on Windows 10 since the beta – is that the grass really is greener on the other side with better support, better security, vastly improved patching and significantly improved hardware migration and support services.
One final piece of advice: other than learning and exploring the full suite of available migration tools, you’d be wise to use small moves to get your teams trained and learn about dependencies you might not now know of. And once you’re comfortable with the process, move broadly.
Oh, and given the next Windows upgrade will be a cloud version of the OS, it might be worthwhile to think about skipping a step and making a move to the Azure Virtual Desktop early. Even if you aren’t usually an early adopter, avoiding that next move could be a decent reason to change that.
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