So yesterday was it. July 29th came and went, and with it the free Windows 10 upgrade window that Microsoft had been dangling (and nagging you about) since last summer. If you were still running Windows 7 or 8.1 and you hadn't clicked that little white flag icon in your system tray by midnight, you're back to paying full price — $119 for Home, $199 for Pro, last I checked on the Microsoft Store.
I did it. Barely. I want to be honest about how last-minute this was: I upgraded my old Dell at around 11:40pm on the 28th, mostly because I kept putting it off and then panicked when I remembered the date. The whole thing took maybe 45 minutes, most of which was just sitting there watching a progress bar creep from "Working on updates" to a series of reboots. No horror stories to report, which honestly kind of surprised me given how much hate that "Get Windows 10" nag tool got over the past year. People called it malware. People wrote entire blog posts about disabling it with registry hacks. I get the frustration, the pop-ups were relentless, but the actual upgrade process itself has been fine every single time I've run it, on three different machines now.
If you missed it, here's where things actually stand:
You didn't necessarily miss your last chance, you missed the free chance through the standard route. A few things worth knowing if you're in that boat:
- Buying Windows 10 outright is still an option, obviously, just not free anymore.
- If you're running Windows 7, it's still getting security updates through January 2020, so you're not in immediate danger, you've just lost the free upgrade path.
- Clean installs from Windows 7/8.1 media using a valid product key from either of those versions have, in my experience over the last year, still activated fine against Microsoft's servers even after upgrading. I'm not going to promise that holds forever, this is anecdotal, not a guaranteed loophole, and I wouldn't be shocked if it eventually stops working.
- If you've got a machine you were on the fence about, this is a reasonable moment to just... not upgrade. Windows 7 isn't going anywhere in the next few years and there's no shame in staying put if your hardware is old or your software depends on it.
One thing I want to flag for anyone who does still go the upgrade route on old hardware: back up first. Not "eh I'll be fine," actually back up. I've read enough forum threads over the past year about upgrades bricking machines with weird driver conflicts, mostly older Wi-Fi chipsets and some HP laptops with proprietary bloatware that doesn't play nice with the new driver model. My Dell was fine. Your mileage may genuinely vary, and Windows 10 doesn't always ask permission before it starts reorganizing your driver stack.
Also, small tangent, but it's been a weird month to be paying attention to tech news generally with everyone's phone screens full of people wandering around parking lots catching Pokémon. My brother-in-law walked into a fountain at a mall in Ohio last week doing this, which is a real sentence I now get to type. I haven't downloaded it myself yet. I probably will, mostly out of professional curiosity at this point, everyone I know under 35 has it open constantly and I want to understand what the fuss is about before I have an opinion on it.
Anyway. Back to Windows 10. If you're one of the people who upgraded in the final rush like I did, go check Settings > Update & Security > Activation just to confirm it actually took. Mine showed "Windows is activated with a digital license" which is what you want to see. If it's showing anything else, or throwing an error code, the built-in troubleshooter under that same menu actually works now, it wasn't always reliable a year ago but it cleared up an activation hiccup on my sister's laptop back in the spring without me having to call anyone.
I don't have a grand take on whether Windows 10 is "good" at this point, a year in. It's fine. It's what I use every day and I don't think about it much, which for an operating system is probably the highest compliment I can give.