This may not have helped your specific case, but I recently bought 1Password, and updated all my security questions with randomly generated 16 character string answers, and just put those strings in the "notes" section of a website. So when they do challenge me I can just copy/paste them in. It's been awesome!
I've used 1Password generated passwords for years. You're right, it is awesome, but only until you have to relay one of those generated strings to a support person over the phone:
"...left curly brace. No, it's like the parenthesis, but squiggly. Are you using a regular keyboard? Hold shift and type the left square bracket. The square one. It's to the right of the P..."
I can't imagine the horror of having to recite any password to an actual human being. What kind of company asks you to tell them your password by phone?
"No, the backslash. The one that leans backwards, no, I mean, to the left. Above the Enter key." Surprise, the backslash is not above the Enter key on Canadian bilingual keyboards.
1Password gladly generates "pronounceable" passwords (e.g. "thax-lers-ponc-werv"). I usually think a bit about whether digits or symbols are required (some services and websites - Skype notably) don't like them.
A 20-char passphrase with spaces, dashes, or character-based (e.g. "S") word-boundary delimiter is often good enough to provide excellent (80+ bits) entropy.
Or how about everybody that uses these fucking inane rules just do something sensible - like lock an account out if there are more than 5 failed logins in a row. Using a setup like that even "4321" is probably secure enough. Obviously use a secure hash on the backend as well.
That's the trouble... the "sensible" options aren't so sensible when you really sit down and think about how they can be dodged, broken or abused.
Imagine I'm trying to crack into your site, and you lock any account after 5 failed logins in a row.
If I have access to (or can guess) a few thousand usernames, I can try the 4 most common passwords on all of those with no problems. I'll probably get some hits, no?
Or heck, I can try the 5 most common passwords, and not only will I have a few hits, I'll also have plenty of time to dig around without any attention from you, because you'll be struggling with a massive customer service nightmare, as thousands of your customers find themselves all locked out the same morning.
Even better is to generate real words. I took a "1000 most common english words" list and reduced it manually to 256 that don't rhyme with other common words and now use that to generate pass-phrases. It's my best solution for English since phonetic spelling isn't a feature of English.
Heh, yeah luckily I haven't had to do that, but I have chosen some obscene answers to them, and then later had to recite, and spell them out to a horrified Indian call center worker.
Well, the implied ethnicity of the poster is non-Indian, so in addition to the embarrassment of having to spell out obscene words, there's the cultural gap as well. The poster can't judge how offended the call center worker was, and probably feels like he's poorly representing his culture. I've had many similar experiences, especially since I've been living in Korea recently, and it's very uncomfortable not knowing exactly how big of a faux pas you committed.
Well he was, and that's part of the story. I wasn't passing judgement on him as a person, or stating that because of that one characteristic he was Evil.
Edit: see my response to shard. No offense intended, and I hope none was taken :)
I use LastPass, but also use generated passwords to answer security questions. For these questions, one can enable the options for only using alphanumeric, unambiguous characters.
