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There were tons of issues with earlier DRM models. SecuROM not working with certain disc drives, SafeDisc driver vulnerabilities, StarForce allegedly bricking some hardware, Tages eating up online activations for simple hardware swaps. Everyone hated them, but the Sony rootkit was probably the biggest one at the time. From what I remember there was no mention of it anywhere on the CDs or in the EULA, and when they did get caught their "fix" basically just hid the files while collecting info on you and sending it back to Sony.
That’s it. All you had to have done to be infected was to have ever popped a disc into a PC drive. Was surprised at the time that the backlash seemed so limited.
Autorun was never a safe feature for Windows or any other system to include. It's been a source of one attack after another over the years. Inserting media should never cause programs on that media to run.
I don't disagree with this statement in general. That days, I don't know how old you are and whether or not you were really around the home PC space when the auto run feature first came to be. I can sort of understand what Microsoft was trying to accomplish with it... the mid-90's were a wild, lawless time with regard to personal computing. There was a lot of heartburn on the end user side because things were changing so rapidly. Getting them to understand that what a "drive letter" was, how to get there, and how to run an application from it (let alone what an application even was) proved challenging even under the best circumstances. The ability to insert a CD into the drive tray and have it "just work" (also a big theme in Win 95/98) was a godsend for a lot of publishers.
Of course, in today's world, we look at that kind of feature and rightly say "yo, that's fucking crazy, why would you do that?", but in the old days it really did help. At the end of the day, it was a useful feature that, like a lot of windows legacy crap, was left in the OS after its usefulness had gone and just became another attack vector.
Thing is, security folks noticed autorun was a problem back then.
The "wild lawless time" was not the context in which Microsoft made those poor security designs; it was a consequence of those designs — which were noticed and criticized by security folks at the time.
Another entertaining example is the demythification of email viruses.
In the early 1990s, email viruses were a myth: the Good Times virus was a hoax that told people that they could get a virus by reading an email. At the time that hoax went around, this was not actually possible: email software just displayed text; unless you downloaded an attachment and ran it, you couldn't get a virus in email. Certainly not just by opening and reading an email.
But then along came Microsoft with Outlook Express, and security vulnerabilities that allowed the action of rendering an email, even in a preview pane, to inject malicious code.
Suddenly email viruses were not a myth anymore; they were everywhere.
I kinda disagree with the context comment though. That era of computing was inherently wild - nobody had figured anything out yet beyond the most basic and general strokes, and security analysts (such as they were) had what would be considered a childish understanding of IT security by modern standards. Heck, Windows95 didn't even have the TCP stack enabled by default, so when these features were being designed, planned, and coded at Microsoft, there was no context for security on that kind of feature. Wikipedia says that Win95 was in the planning stage in 1992 - I take that with a grain of salt, but the concept is valid. Microsoft was writing the core features of Windows 95 before WAN was even really a thing. Like I said, I don't disagree with the idea that AutoRun was a terrible thing among many terrible things Microsoft is responsible for, but given the era in which AutoRun came out, it was a reasonable trade-off between security and functionality for the lowest common denominator of user. The whole thing should have been disabled (on 95 and 98) when Windows 98 came out since they should have known better at that point.