IDK, I think it's been a bit of a (reverse?) bell curve of sorts.

30+ years ago, You had to be a -lot- more careful about how you handled releasing software. Your stuff was in boxes on shelves, most people didn't have internet access to 'download an update' so fixing anything had a long tail support cost (i.e. paying for the media containing the fix and shipping).

But there's a fine line. As an example, If your shop is having a vendor do brand new stuff, -compartmentalized from your other stuff-, using technologies that are actually out of support vs an in-support version is a free/zero effort update versus using the outdated stuff... Something went wrong on the management side.

Exactly!

How many updates did one apply to Windows 3.0 and Word in those days??

Sure, there might have been a “hotfix” available for download over a long distance BBS, but virtually nobody would have ever done so (even if they were lucky enough to have a modem). Maybe large companies applied such when impacted.

Even in the Windows XP days, I think windowsupdate.com was still a manually triggered process…

For a while, bundled drivers were a steaming pile of crap in quality and several generations of Windows suffered greatly until Microsoft got vendors in line and updates became common.

> Your stuff was in boxes on shelves...

Have you ever heard of an SLA? This "used to be" story about software has never been true. If you can't meet the agreement, then or now, you're done.

Software has always been a lot more diverse than just consumer goods. Why is that your only evidence of how you think software projects are managed?