July 4 fix-it weekend: Last chance to do free Windows 10 upgrades for the family

This is the last holiday weekend before Microsoft's free Windows 10 upgrade is gone in a flash. Are you prepared? Here are some tips to make the process go more smoothly.
Written by David Gewirtz, Senior Contributing Editor
Stephanie McCabe via Unsplash, modified by the author

Heads up, IT folks. Today is June 30. That means there are only 30 days left until the free Windows 10 upgrade goes away.

Making matters worse, we are about to enter the July 4th holiday weekend. Holiday weekends, as most readers of this column know, are the internationally accepted times when families demand that their techies fix their computing and technology problems.

Yep, before you get that second hot dog, or pile into the family car for the trip to your family's favorite fireworks-watching spot, you better get those family computers fixed.

Otherwise Mom and Aunt Molly will have to wait until Labor Day or worse --- the holiday the Constitution specifies is dedicated to computer repair all across the country: Thanksgiving.

This holiday weekend is a bigger deal than most. This is make-it-or-break it time for Windows 10 upgrades. This is the last time you'll be able to upgrade everyone's PC to Windows 10 for free.

When it comes to Windows 10 upgrades, you don't have until National Fix Mom's Computer Day. We are nearing the end of the free Windows 10 upgrade experience. After July 29, if those of you eligible for free Windows 10 upgrades do not upgrade, you'll have to pay a hefty fee to move old Windows 7 and Windows 8 machines to Windows 10.

It's this weekend, or Mom's going to be staying on Windows 7 until she needs a new computer (which may well be a Chromebook).

While you'll always be able to upgrade Windows for a hundred bucks or so, the fact is that's a tough expense to convince your friends and family to eat. Rather than spending more than a hundred bucks on a Windows upgrade, there's a good case to be made for moving Aunt Sally to a Chromebook or Cousin Jeff to an iPad.

There is always some risk any time you do a major OS upgrade. We decided, for example, not to update my wife's beloved Samsung Series 9 ultrabook from Windows 7. A search for "Samsung Series 9 Windows 10" shows a long stream of users with driver issues, particularly when it comes to the keyboard and trackpad.

Not all machines can be upgraded to Windows 10, so do your research before kicking off that upgrade. Additionally, anyone running something older than Windows 7 can't make the jump, at least without first upgrading to a sacrificial Windows 7 or Windows 8 license.

It's been my experience that downloading and upgrading Windows is a 2+ hour process. To save yourself some time, you might want to go to Microsoft's Windows 10 download site and download an ISO image you can bring it with you when you go on your service call, uh, family visit.

Make sure you pack along a backup drive like one of the ones I reviewed recently. I like these SSD-based drives because they're fast, and that means you'll get done faster, possibly even before the potato salad is gone.

The bottom line is pretty simple. If you don't upgrade your family this weekend, they'll either be stuck in older, increasingly less secure versions of Windows, or setting themselves on a course to an alternate computing paradigm.

Finally, if I were you, I'd pack along a spare, cheap Chromebook just in case. I've got three of them and I've taken to bringing one along to family events, just in case an upgrade goes terribly wrong or it's not possible to repair a computer after Dad tried to "fix it" using a hammer and screwdriver.

If worse comes to worst, you can power wash the Chromebook and get your family member set up and back online in a matter of minutes.

And, hey, stand your ground. You have a right to at least one slice of pie and a second hot dog. No upgrades or fixes until the geek gets fed.

Windows 10 Anniversary Update: Take the preview tour

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