# How secure is choosing one out of N generated passwords?

I'm looking to generate some new passwords for myself that are easy to remember, but hard to crack. By choosing a generation algorithm and generating one random password with it, I can be relatively confident of how hard to crack my password is. (I can calculate its entropy.)

If, instead, I keep generating passwords until I see one I like, the security of my password is (significantly?) less. Worse, because I can't analyze my own mind like I could analyze an algorithm, I don't even know how insecure my password might be. It should be better (in terms of security) to control myself and say, before the password is generated, "whatever password is generated is the one I will use". But it might not be as easy a password to remember as "correct horse battery staple". It's hard to predict what will be easy/hard to memorize, and it can vary a lot from person to person.

What about a happy medium, where I decide that I will generate exactly N (for example, 10) random passwords, and choose one of them? Would this be any worse than "1/N times" secure?

• This depends on your selection criteria - if for example you pick something that you can type with only your left hand (quite a common choice), it could significantly reduce the strength of a password. For your "happy medium" suggestion, I think your reasoning is correct on average, however there could be some significantly less than average passwords chosen like that as well – user2813274 Jul 16 '14 at 19:12
• True, if I'm generating series of words, and for example a grammatically correct phrase shows up and I choose it, I'm hurting yourself. On the other hand, if I decided on choosing the first password to show up and it was grammatically correct, isn't it a similar problem? And pretty unlikely? And in some cases, by generating more than one password, I could avoid some obviously insecure passwords in the rare chance that they show up. – Dan Getz Jul 16 '14 at 19:33