How long is a password string?

2011-10-18 by grahamlee. 1 comments

Password policy questions are a perennial fixture of IT Security stack exchange, and take many forms.

Take, for example, the recent XKCD comic on the subject:

Shortly after it was posted, user Billy ONeal asked directly whether the logic was sound: Is a short complex password or a long dictionary passphrase better? You will find answers that support either conclusion, as well as answers that put the trade-offs involved into context.

Of course, part of knowing how easy a password is to crack is knowing how a password cracker works. Are there state of the art techniques or theory specifically for attacking pass phrases? Are there lists of the most common words or ngrams used in passwords and pass phrases?

So we’ve got no consistent idea about what constitutes a “good” password, although we can probably guess at what weak passwords will fall first. But then who is responsible for deciding a user’s password strength? Pretend for a moment that we agree what a strong password is. Should we stop users from choosing “weak” passwords, or is it their own fault for not understanding information theory and the entropy content of their chosen string of characters?

The definitive answer is “it depends”. It depends on how valuable the assets being protected by password access are. It depends on whether the value is appreciated by you as service provider/systems administrator, or by the user as customer/asset owner (or by a combination of those roles, or by someone else). It depends on how much inconvenience you’re willing to put your users to, and on how much inconvenience your users are willing to accept.

So, you’ve decided that you do want to enforce a policy. How does that work? Some websites enforce a maximum password length, is that a good idea?. Should passwords be truly random?

To summarise the discussion this far: there are different ideas of what makes a good password, of who is responsible for deciding whether a password is good or bad, and of how to enforce good passwords once you do decide you want to. But all of this discussion has already put the cart before the horse. Are your passwords going to be brute-force, or will the attacker use a key logger? Maybe they’ll attack the password where it’s stored?.

Indeed, while we’re asking the big questions, why passwords at all? Might biometric identification be better? Why not just forget all of this complication over strong passwords and start taking fingerprints instead? Some reasons include the possibility of false positives from the biometrics system (who hasn’t tried holding up a photograph to a facial recognition system?), and the icky disgustingness of some other attacks.

Suffice it to say that the problem of password security is a complex one, but one that the denizens of enjoy tackling.

QotW #9: What are Rainbow Tables and how are they used?

2011-09-09 by roryalsop. 0 comments

This week’s question, asked by @AviD, turned out to have subtle implications that even experienced security professionals may not have been aware of.

A quick bit of background:

With all the furore about passwords, most companies and individuals know they should have strong passwords in place, and many use system enforced password complexity rules (eg 8 characters, with at least 1 number and 1 special character) but how could a company actually audit password strength.

John the Ripper was a pretty good tool for this – it would brute force or use a dictionary attack on password hashes, and if it broke them quickly they were weak. If they lasted longer they were stronger (broadly speaking)

So far so good, but what if you are a security professional emulating an attacker to assess controls? You could run the brute forcer for a while, but this isn’t what an attacker will do – maths has provided much faster ways to get passwords:

Hash Tables and Rainbow Tables

Hash Tables are exactly as the name sounds – tables of hashes generated from every possible password in the space you want, for example a table of all DES crypt hashes for unsalted alphanumeric passwords 8 characters or less, along with the password. If you manage to get hold of the password hashes from the target you simply match them with the hashes in this table, and if the passwords are in the table you win – the password is there (excluding the relatively small possibility of hash collisions – which for most security purposes is irrelevant as you can still use the wrong password if its hash matches the correct one). The main problem with Hash tables is that they get very big very quickly, which means you need a lot of storage space, and an efficient table lookup over this space.

Which is where Rainbow Tables come in. @Crunge‘s answer provides excellent detail in relatively simple language to describe the combination of hashing function, reduction function and the mechanism by which chains of these can lead to an efficient way to search for passwords that are longer or more complex than those that lend themselves well to a hash table.

In fact @Crunge’s conclusion is:

Hash tables are good for common passwords, Rainbow Tables are good for tough passwords. The best approach would be to recover as many passwords as possible using hash tables and/or conventional cracking with a dictionary of the top N passwords. For those that remain, use Rainbow Tables.

@Mark Davidson points us in the direction of resources. You can either generate the rainbow tables yourself using an application like RainbowCrack or you can download them from sources like The Shmoo GroupFree Rainbow Tables project website, Ophcrackproject and many other places depending on what type of hashes you need tables for.

Now from a defence perspective, what do you need to know? 

Two things:

Longer passwords are still stronger against attack, but be aware that if they are too long then users may not be able to remember them. (Correct Horse Battery Staple!)

Salt and Pepper@Rory McCune describes salt and pepper in this answer:

A simple and effective defence that most password hashing functions provide now is salting – the addition of a per user “salt” value stored in the database along with the hashed password. It isn’t intended to be secret but is used to slow down the brute force process and to make rainbow tables impractical to use.  Another add-on is what is called a “pepper” value. This was just another random string but was the same for all users and stored with the application code as opposed to in the database. the theory here is that in some circumstances the database may be compromised but the application code is not, and in those cases this could improve the security. It does, however, introduce problems if there are multiple applications using the same password database.

QotW #1: How does changing your password every 90 days increase security?

2011-07-15 by roryalsop. 2 comments

Question of the Week #1

How does changing your password every 90 days increase security? As selected by @HendrikBrummermann this has been one of our more popular posts, with discussion on the reasons for password expiration:

  • To mitigate the problems that would occur if an attacker acquired the password hashes of your system
  • It prevents people who use the same password for everything from getting your system compromised if their password is figured out somewhere else
  • Compliance reduces the risk of penalties of non-compliance (thanks @AviD)
  • By resetting password every X days we are telling the user – Hey, this is important and it should not be taken lightly

and Against password expiration:

  • Your password, and the attacker’s guess at your password, are independent. The probability that the attacker’s next guess is correct is the same even if you change your password first.
  • Nothing encourages passwords on post-its quite like frequent expiration, especially if there are also high complexity requirements
  • It annoys users
  • They end up having to work out a new password – which research shows is often is derived from the previous one in a way that is very easy to crack nearly half the time
  • You can expect additional support costs to cover users who have forgotten

How to balance the pluses and minuses depends on your organisation’s risk profile and other requirements.

An alternative to password expirations is requiring stronger passwords, and we have questions and research on that also.

The associated question – Why do sites implement locking after 3 failed attempts – details another aspect of the defence against brute forcing, and discusses why 3 may or may not be a suitable number.

These questions, answers and commentary are well worth a read if you are trying to set a password expiry policy in your own organisation, or want some background as to the risks.

A tour of password questions and answers

2011-07-06 by Neal McBurnett. 1 comments

According to Rory Alsop’s post the most popular topic at our IT Security site is passwords.  So in this post I’ll provide a tour of some relevant questions and answers, and a look at how it sparked further investigation of the sorry state of password protection in some current systems.

There is an amazing amount of confusion, disinformation and bad practice out there with respect to password management.  This is all the more frustrating because the basics were worked out back in the dark ages (1978 to be precise) for Unix by Bob Morris and Ken Thompson (Password Security: A Case History, Morris & Thompson, 1978). They not only covered the importance of hashing passwords with salts and a slow algorithm, but they described what is now called a “pepper” (a second salt stored apart from the password database).

So if you peruse the dozens of ‘passwords’ questions you’ll find frequent reference to the basics.  We’ve also tried to summarize some of the key points in the ‘passwords’ tag info.  By the way, that’s one of the cool things about StackExchange sites in general – how they provide for a little “wiki” for each tag, to allow us to put key information just a mouse hover or one click away from readers.

Of course even among good practitioners, there are debates about the finer points, and that is another thing you’ll find here.  See e.g. the spirited conversation about highly iterated password hashes for web apps vs the risk of DDoS attacks at Do any security experts recommend bcrypt for password storage?.

In the end, you’ll often find that the right approach depends on what kind of “security” you’re looking for.  As our Frequently Asked Questions points out, this depends on context – what assets you’re trying to protect from what sorts of threats, how your different vulnerabilities compare, and how that all fits into your business plan.

I’ll end with a look at one question which demonstrates the kind of expertise we have already attracted to the site: MySQL OLD_PASSWORD cryptanalysis?.  I asked this after stumbling across some other questions about how MySQL used to deal with passwords.  To my amazement, within hours, noted cryptographer Thomas Pornin had not only cracked the old algorithm, but he included some code to demonstrate just how totally broken the OLD_PASSWORD scheme was.  Subsequently we also found a paper from 2006 with more details.  Evidently the folks at Oracle who work on MySQL hadn’t gotten the memo then, and still have a lot of work to do to improve their current scheme, as described at Looking for example of well-known app using unsalted hashes.

So stay ahead of the crowd: when you have a question about security, see if we have a good answer.  If not, ask away.  And if you see questions that need more work, please contribute to providing good answers!