Computer Things Going Wrong 01
A potpourri of oops moments from the Good Old Days of I.T. All from memory, so some details may be suspect, but the core story is correct.
I know what I meant….
This must have been back in the early days of Windows 3.1. From memory, it wasn’t a Microsoft program and was something where you were inputting data and so you didn’t want to lose your work. All of a sudden this popped up:

Mmm. Yes to Cancel the program (and probably lose all my data) or Cancel to Cancel the program (and probably etc.)? Paradox.
In a case of I Know What I Meant, the programmer probably meant Cancel as in Cancel this little pop-up, return to the program and take your chances.
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When those Interactive Voice Response (IVR) systems first came in, I recall one place trying to Do The Right Thing (great film, BTW). But their first message/instruction, when you called their number, was something like “If you don’t speak English, press One“
Remove the Floppy
IBM set up a lab, in the USA, to test out their new ‘self-install’ instructions. Again this was before PCs took off and was for small, multi-user systems to be deployed at remote locations. Clerks and managers would do the install (!).
The lab, with their permission, filmed such users testing out the instructions. One step said “Remove the floppy disk from its protective jacket”
Here is what IBM called a ‘floppy disk’ in the 1980s:

They came in a half-envelope thingy (the “protective jacket”), but were not obviously ‘floppy’ nor a ‘disk’, They were sorta firm and square, with the disk safely (mostly hidden) inside.
So, a number of users in the Lab were filmed carefully unpicking the seams of the square, removing the ‘floppy disk’ from said square casing and trying to slide it into the reader.
IBM changed the wording.
The (apparent) Bug that Cost the Customer Days
The IBM system I cut my teeth on was fantastic, but it had a big, potential flaw. If you lost one (1) hard disk, you lost everything; operating system, programs and data. You had to back up regularly. This was before PCs/Servers took off. As it was a ‘midrange’ (departmental/small-business) system, then lots of people would be impacted if it was down.
So IBM brought in a complex new disk protection mechanism called Checksum. From memory, it was a form of RAID, but no matter. The upshot was it was brand new and the first major customer to implement it, would have to take things really carefully. If, during the setup it went wrong, everything would be wiped on the drive or otherwise rendered useless.
My memory it was two very careful and experienced guys doing the work, and doing so at night. One from IBM, one from the customer. Cross-checking each other’s work, before going on to the next step.
They came to a key Yes/No decision and both swore they said No. But the system did it anyway and ruined all the data. It took days to recover.