In doing medical transcription I've found myself making insidious typos that the computer doesn't catch, e.g. "food" for "foot", or "hell" for "heel." I've got "hell" changed to "heel" in my shortcut software, but this has resulted in spelling Etiquette Hell as Etiquette Heel.
I did that recently.
We had an event at work that was my job to coordinate. I'd created and printed the logistics, which included the Dean introducing a particular keynote speaker at the podium.
The keynote speaker's first name: Kevin. What I typed: Devil. I did not notice it until the Dean's executive assistant started giggling hysterically when I gave her the logistics and asked if I had something against Dr. "Devil" Jones..
I at least corrected the logistics before the Dean saw my typo.
Years ago, back when computers were brand new, I was a secretary. One of my jobs was to type up minutes for a particular meeting, a meeting that I thought was a complete waste of time. The departmental higher-ups agreed, but since it was a hospital regulation we still had to do it.
Well, once I typed up one set and sent it along to the clinic's highest ranking enlisted person. He brought it back, and he was laughing. I don't remember what the original line was, but I had typed, "This report is rot to fulfill the requirement (etc.)" This early computer didn't have a spell checker, but I don't think it would have caught this anyway since I hadn't misspelled anything. The sergeant said, "I know you think typing this report is a waste of time, but we really shouldn't say so."