Yeah, I'm in the IT dept (companys conatantly flop between throwing software into engineering, IT, or its own dept) and the other day, 5 minutes before I leave for a week long vacation a user comes up and asks if we're ignoring her.

Outlook is constantly asking for a password to one of the emails she uses. She doesn't know it and keeps clicking close on the popup. So she sends an email, FROM THE ACCOUNT SHE IS LOGGED OUT OF, to helpdesk a few days earlier.

Why on earth are you putting double quotation marks inside double quotation marks? We have single and double quotation marks for this exact reason. It took me forever to understand what you're saying

I've had to walk someone over the phone through a prompt that says "Click OK to continue" and there was nothing else except the OK button.

Also when I used to work for Federal Student Aide help center it was common for (people who were about to enter into higher education) to get stuck at the end of the online form when a final screen came up with the options "Submit" and "Cancel"