The world is expecting information about a new major Windows release on June 24. I’ve been watching the byplay and discussion of what could be new, and what might be next. For me, one question is paramount. Will the next upgrade be free? Or, will users have to pay for that privilege? That’s what has me pondering free Windows upgrades, as the Microsoft event comes in a just a few more days.

History  Guides Me, In Pondering Free Windows Upgrades

Let me think back on my own personal Windows history. I remember most early upgrades to Windows were neither free (because they came on “official media”) nor terribly expensive (because MS wanted users to stay current). If I remember correctly, upgrades cost US$50 to $99 for Windows 3.0 and 3.1. Windows 95 upgrades listed for US$109.95, but deals were sometimes available. Ditto for Windows 98, which also offered a pre-order price of $94.99 for upgrades to those willing to spend less sooner and get the media later. Windows Vista is the last version that I remember Microsoft charging a fee to upgrade and it cost more: US$120 (Home), US$200 (Business) and US$220 (Ultimate).

Since then, upgrades to 7, 8, 8.1 and 10 have pretty much all been free to those with legit, valid Windows licenses for previous (and sometimes older) versions. To my way of thinking, this says that recent history argues that a “next upgrade” should be free for Windows 10 licensees. OTOH, there’s plenty of older history that argues directly to the contrary.

Time Will Tell … and Soon, I Hope!

With a major announcement coming up on Thursday, June 24, we may soon be finding out what any upgrade deal will be for Windows 10 licensees. Because I have 10 PCs here at Chez Tittel, I’m more than a little interested in (and apprehensive) about the upcoming upgrade policy. In the meantime, I’ve got my fingers crossed that recent history trumps ancient history now that physical media are seldom needed, and OS downloads represent the most common and widely used distribution channel for Windows install files.

As the community of Windows Insiders, journalists, watchers and hangers-on collectively holds its breath for June 24, I’m thinking about an old Tom Petty song. The name of the song, of course, is the 1981 classic “The Waiting.” The lyric runs “The waiting is the hardest part.” And wow, how true is that as time marches toward Microsoft’s next generation Windows event on June 24. For me — and I imagine, many others — Tom Petty got Windows wait right.

Because Tom Petty Got Windows Wait Right, Hang In There!

Earlier this week, a leaked version of what purports to be the next Windows release appeared online. Since then, all the usual Windows news outlets are abuzz.  These include WinAero, Windows Latest, Windows Central, OnMSFT, Thurrott, and countless others. All are awash in exposition and analysis of “what’s in there.”

Visit one or more of the widely read third-party Windows sites to see what I mean. On every one, stories about the leaked version dominate their home pages.  Here’s a quick “count analysis” of what I see. In fact, most of them have devoted over half their line items to this topic. Some go as high as 90 percent.

When the Hardest Part Is Over, Then What?

I’m crossing my fingers that MS will indeed release an official next-gen version during or after the June 24 event. Because I’m an Insider MVP I’m not allowed to write about details regarding leaks and unofficial releases, hacks and other similar stuff. That probably explains why I’m a little frustrated that there’s so much activity already underway that I can’t dive into just yet.

In the meantime, I’ll keep humming Mr. Petty’s tune and watching the clock. There’s really not much else I can do right now — except, of course, to keep plugging away at all the real work I actually get paid for. Do stay tuned: as soon as I can, I’ll start covering this next big Windows thing, whatever it turns out to be.