How does 1Password know if a website is asking a personal question instead of a password?

@clay454 - What you're describing are called Security Questions, and they should long ago have gone the way of the dinosaurs, since they’re terrible security. The fact that banks (of all places) still use these is both terrifying and an indication that they are among the most backward-looking, resistant-to-change organizations around.

The main problem with so-called Security Questions is that they're easily discoverable. Anyone at all can visit your account from any computer, claim they "forgot the password," and then enter one or two questions that are supposed to "prove" you're you, but in reality could be quite easily discovered by anyone who really wanted access to your account. The longest, strongest password in the world won't protect you if someone can click a button to bypass it and answer a set of much less secure, easier to guess questions instead.

However, there are things you can do to make the process less dangerous from a security perspective and also more fun: for one thing, see if you can turn these security questions off. You may not be able to, but some websites allow you to adjust your settings to turn them off. Might be worth poking around in the site's settings. If you can't turn them off, then you'll have to outsmart them. What do I mean? Well, what would you say if I told you that my mother's maiden name is 4#JjSLzvjd%Qr$g$nCBCv ? Or that the name of the street on which I grew up is D+zy$P7B8r2bK^hq ? (please note: these are examples generated just for this reply, not my actual answers).

You can actually use 1Password to help you generate random passwords for each of the "security questions," instead of giving the real (and easily discoverable) answer. When you sign up, just place your cursor in the answer field for each of these questions, and then use 1Password’s strong password generator to create a string of gibberish like I did above, and remember it for you. Like this (note: it should go without saying that the below is also just an example; Wendy is fictional and Facebook does not make you answer security questions):

1. Click the Edit button on the login record in question (if you already have it saved. You'll see an example section for new information, with a sample label and new field, like this:
   
2. Give the first label a name like Security Question 1 and the "New Field" the text of the question, then give the next line's label a corresponding title, like Security Answer 1. Then click the gray circle with the three dots to the right of the field and set the field type to Password:
   
3. Doing this will change the field type to a password, and you'll be able to click the password generator button to create a nice long string you won't have to remember:
   

Repeat this for the other "security questions." When you're finished, you'll have something that looks like this:

So, next time you return to the site, you can simply copy and paste in your "answer" to any random "security questions" the site makes you answer, and stay secure while doing so!

@clay454 - you're quite welcome! Glad it was helpful. :)

@XIII -- it's true. Most of the time, that's not the case, but I have had to explain to a bemused operator why I was giving her thirty characters of nonsense for my first grade teacher's name. ;)