Assuming that you are allowed to type an answer.
United Airlines makes you pick from a list of pre-selected answers. And some of the questions are easily worthless.
For example, one of the United "security" questions is "What is your favorite ice cream?"
How is someone who is lactose intolerant supposed to answer that? Or someone who has never had ice cream? Or someone who doesn't like any of the flavors on the list? My favorite ice cream today isn't the same as it was 20 years ago when I signed up for my frequent flyer card.
Harvard University
Heck, I tried teaching her to write down her passwords in a notebook, and she either keeps forgetting to write down, or she loses the notebook completely.
Thankfully, my LastPass writes down my passwords for me and is impossible to lose physically.
I called into support. This was not my first call, but it was the first call where I was prompted for the security question by the rep. And, there was no mention that it was a security question, just "So deathanatos, what color is the dress?" (Not the actual question, of course.) I was like, "uh, what?" at which point the rep. mentioned it was the security question. I'm already logged in, so I dug around the account settings, and found that under there, the security questions and their answers were visible, so I rattled off the answer at that point.
That particular method of support contact required you to log in, too, so anyone in contact could "answer" the security question by just looking it up…