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Re:Why Johnny Won't Upgrade by scarface74 on Thursday August 27, 2020 @09:49AM (#24293639)
I have been in IT for over 20 years now. I have had orders of magnitude more problem with updates than with malware/viruses/hackers.

Until you get hit by this....

https://www.giac.org/paper/gcih/201/microsoft-iis-superfluou...

It was the first widespread IIS vulnerability that almost hit me. The tl;dr version: All you had to do was encode a shell command in the url bar if the site was running IIS and it would execute it on the server.

Re:Why Johnny Won't Upgrade by unionpivo on Thursday August 27, 2020 @10:50AM (#24294223)
Oh we(organizations I have worked for) have been hit several times (not IIS, but once it was several wordpress sites we used, once it was outlook, once we never figured out - probably inside job, ... ). But that was 3, 4 times in 20 years.

Updates its 3,4 times per year. Like I said order of magnitude difference