I work in IT and I can assure you that software developers have been doing their best for the past 20 years to live up to that expectation.
I can't quite put my finger on why I can't adapt. It's some combination of the facts that 1) there's often a huge dump of information, much of it so technical that it's useful only to the developers, 2) it's fairly rare that it offers a truly useful suggestion, and 3) many of the messages I encounter ask me to do something that makes things easy for the developer rather than the user (update the software, contact the manufacturer).
I think it's something we as an industry ought to work harder on, because I don't think the failure is only in the users. I think, although I can't explain exactly why, we're communicating very poorly.
No meaningful indication what file was locked. No meaningful indication what was locking the file. The process simply stopped.
It got much better after Win 8 onwards.
So much this.