“Oh, it’s segmented. You have to download this program to expand those. It’s called WinRAR. Way better than WinZip.”

“Do we have to pay for it?”

“No…but if you’re as cheap as I think you are, it’ll keep bugging you to for a quarter century until, in the grim darkness of 2023, Windows 11 finally supports the format natively.”

In retrospect, my friend’s comment was amazingly prescient. How could he know how grim and how dark the future would be? How could he predict that Windows would switch back to sequential numbering, but skip 9? And how did he know that I am so, shall we say, thrifty that rather than paying $30, I would wait for more than two decades just trying to get my task done in WinRAR fast enough that the “Please purchase WinRAR license” pop-up didn’t have a chance to appear?

Yes, it has taken the better part of three decades for the .rar file to finally be supported in Windows without any kind of additional software. Back in the ’90s, it was just one of several competing compression apps (or “applications” as they were called back then) used to shrink collections of files so they could be more efficiently transferred over our woefully slow internet.

How long did it take for us to download the Star Trek set of screensavers for After Dark from the dial-up BBS, using the telnet app WhiteKnight, you ask? Overnight. It was, after all, a shade over 5 MB. But had it not been a .sea (self-extracting archive) courtesy of Stuffit, we would have been waiting well into the next day.

Yes, compression was a must back then, in my case as a young software pirate but of course in more legitimate ways like software distribution and actual “archival” purposes. I can’t speak to whether WinRAR was as common among enterprises as it was among procurers of illicitly duplicated games and applications. But the fact that it has lived a full 30 years since its original development as a DOS program (28 since it arrived on Windows) — up until its most recent release last week, and still nearly small enough to fit on a 3.5″ hard floppy — suggests it found its niche.

As time has advanced, however, the necessity of apps like WinRAR has diminished, as both drive capacity and network bandwidth have increased exponentially. The handful of megabytes that once took me overnight to download and represented a considerable proportion of my hard disk are now the bare minimum to transfer in a single second if you want to call your connection “broadband.” Furthermore, open source standards and options have proliferated, such as the libarchive project.

Then, at some point, someone at Microsoft must have gotten fed up with rushing their .rar operations the way I have for 20 years and thought there must be a better way. And so, under the subheading of “Reducing toil,” they have a few helpful UI updates, then casually and apropos of nothing, this:

    In addition…

    We have added native support for additional archive formats, including tar, 7-zip, rar, gz and many others using the libarchive open-source project. You now can get improved performance of archive functionality during compression on Windows.

Of course, the library has been integrated with other OSes for a long time, and native support for .rar files is old hat for many. But for me personally, this change is epochal.

I have still found uses for WinRAR over the years, some legal, some…perhaps not so legal. And it has never been lost on me that, in the midst of my piracy, I was doubly a pirate, for I was several decades past the end of my 40-day WinRAR trial period. When my alacrity was lacking (my APMs have fallen of late), I would see that nag screen and think: Am I really that petty? Will I really continue to abuse this poor shareware for my entire life? When will I set myself upon the straight and narrow once more (if ever I was on it to begin with) and make an honest app of WinRAR?

Reader, I purchased WinRAR.

It seems only fair that I pay the cost of a coffee — as you know, about $31 these days — to support a piece of software that is among very, very few to travel with me for much of my computing life. Few other programs have been as constant a companion, though I would pay for Winamp if I could.

(Plus, I haven’t updated to Windows 11 and won’t until there’s no other option, so I don’t have the benefit of this particular integration.)

I don’t know what the future holds for WinRAR; I’ve asked the company what it thinks Windows officially adopting the format will mean for its software and business and will update if I hear back.