Your description made me think of Goto Fail:
https://www.imperialviolet.org/2014/02/22/applebug.html
or using logical instead of boolean (or vice versa)
logic
I did find this:
https://arstechnica.com/gadgets/2021/07/google-pushed-a-one-character-typo-…
But I'm pretty sure I recall another similar bug of this type.