[Cushman]

But it falls into the same boat as any dictionary attack. Most people with a passphrase are probably going to use one from a song. 90% of them are going to use one of the top 1,000 songs, 90% of them are going to start at the beginning of a line. If we say there are ~20 unique lines in the average song, and most people won't use more than ten successive words even if it bridges a line, that's 1000 * 20 * 10 = a keyspace of 200,000. Trivial.

What this means is even if you decide you're going to be really secure and pick, say, the 30,000th most popular song, assume all songs have 200 unique lines (to account for sensical starting points in the middle of lines), and use 20 words from it, you're in a keyspace of only 120 million, which even if it takes 1ms to hash will be cracked in a day.

By contrast, four random english words chosen from the 2,048 most common has a keyspace of ~1.75e13, or 17,500,000,000,000.

Choosing a clever, unusual line from the middle of a very uncommon song is the passphrase land version of choosing a rare English dictionary word and replacing the vowels with numbers. If your hash gets compromised, it might as well be "password".

[moe]

There's an easy way to defeat this:

   smellz like T33N SPIRIT!

Trivial to memorize. Unlikely to brute force.

I use phrases like that for the few locations where password managers don't reach (i.e. the password manager master password).

[Cushman]

>.<

How is this an improvement? I now have to remember a song lyric, and some set of random manipulations of that song lyric. I've used that trick for passwords before, and it was a hassle. But that doesn't even matter— unless you're choosing the manipulations randomly (which is a contradiction in terms) you're falling right back into the exact damn trap the comic was about!

You've added ! at the end, replaced s with z, capitalized some words, and replaced vowels with numbers. These are already standard manipulations in a dictionary attack. And it's causing you to ignore the fact that you've chosen what is probably among the top 10 song lyrics used. "p4ssw0rd!" is "password" as far as a dictionary attacker is concerned. Calling this trivial to brute force is demeaning to the word "trivial". Your attacker wouldn't even laugh at you, because there'd be dozens of other hashes in the file just like yours.

It's been said over and over in these comments: the appearance of randomness is not randomness. Humans are horrible at making things random, as you've just demonstrated. Stop trying to make it look weird, and actually do the math.

[moe]

It's fairly easy for me to remember those manipulations. But you're right insofar that this would probably be both safer and easier to remember:

   Smells like teen spirit, and I like that plenty mucho!

I'm too lazy to do the math on it, perhaps you can help out?

Edit: It's a little annoying to collect these downvotes from people who either haven't done the math themselves or are too lazy to explain their advanced attack methods.

In my naive opinion my string above is at least equivalent to a 12 character password from a set of "Mixed upper and lower case alphabet plus numbers and common symbols.".

I count each word (10) and both symbols (,!) as a character here.

According to [1] an 8 char password of that type would take 83½ Days to crack in a Class-F attack ("supercomputer"). I'm purely guessing that those additional 4 "chars" should put it well into the multi-year range, under the premise my other assumptions are not too far off and that the number of english words is quite a bit larger than the number of ascii characters/symbols.

Any of the downvoters care to debunk that with real math?

I'd be honestly curious about a worst-case analysis that assumes the fragment "Smells like teen spirit" does appear in the attackers dictionary.

[1] http://www.lockdown.co.uk/?pg=combi

[Cushman]

Yeah, that's what I was getting at. Something like that is pretty much immune to naive brute force, even if we count "Smells like teen spirit" as a word. My guess would be that if it does get cracked, it would be by searching [lyric]+", and"+[some kind of Markov attack], but I honestly have no idea how one would work out the entropy in that model. It depends a lot on how the search is carried out, I think.

I guess we'll find out when passphrases become common :)