Crackers report great news for 1Password 4

To understand why this is really good news for us and for 1Password users, it is important to know what “crack” means in this context. I’ll come back round to that and why we encourage the developers of hashcat, John the Ripper, and cryptohaze to take a crack at 1Password. But first, let’s talk about this news and what it says about your password security.

Cracking fast and slow

If someone gets your 1Password data, they will not be able to decrypt it without your Master Password. A determined attacker might then try to guess your Master Password. Your job is to pick a good Master Password so that it will take trillions of guesses before the attacker finds the right one. Our job is to make sure that they can’t make millions of guesses per second on common hardware, thus significantly slowing down the guessing process, ideally to the point of futility. We do our job by using a “slow hash” for deriving encryption keys from your Master Password. In 1Password 4, that slow hash is PBKDF2-HMAC-SHA512. For the Agile Keychain Format it is PBKDF2-HMAC-SHA1.

keep calm

Jens Stuebe, the developer of a password hashing system called hashcat, has been testing just how many guesses per second he can get out of hashcat for the 1Password 4 data format. The hashcat demonstration showed fewer than 500 guesses per second, but with somewhat beefier hardware and a more realistic data file, a better estimate based on the hashcat data would be between 5,000 and 20,000 guesses per second. For all of the calculations below, I will use the more pessimistic (for us, the defender) estimate of 20,000 guesses per second. It’s not because I think the pessimistic estimate is the most realistic, but simply that it is better to err on the side of caution.

If you use a four word password from the scheme described in Toward Better Master Passwords, then at 20,000 guesses per second it would take more than 5,600 years for a high-end PC with with multiple graphics processing units (GPUs) to work through all of the 3.65 trillion equally possible passwords. Of course, the attacker won’t have to try all of those. On average, she will find the right one after going through about half of the possibilities. So the average time to crack will be about 2,800 years. If you use a five word password, then the average time to crack will be more than 20 million years.


We like crackers

With enough time (perhaps far more time than the life of the universe) it will always be logically possible to guess a Master Password. This is simply the nature of the beast. We need to know how many guesses an attacker can make in a second, a day, a year with the resources available to them so that we can devise the most effective defenses against these sorts of attacks.

We make our own estimates, but the best estimates come from looking at real data. We will, on occasion, run our own tests but the people who specialize in password cracking are the people who perform the most stringent tests and will look for things that we might not notice. We want to know how hard they have to work at guessing passwords. We are extremely supportive of projects like John the Ripper, hashcat, and Cryptohaze. Indeed, conversation with people involved in these projects has very much helped us develop better resistance to password cracking.

This is one of several reasons why we are open about our data format. We get better analysis from the security community by doing so. Hashcat, and John the Ripper, worked against some sample data we make available to the public.

Cracking isn’t breaking

When crackers develop tools to guess at 1Password Master Passwords, they are not “breaking” anything. They aren’t exploiting vulnerabilities. They are just automating password guessing. Because they are working directly on the data files themselves, not with the 1Password software, things like lock-outs after multiple failed guesses aren’t an option (and don’t provide any meaningful security against encryption tools like this).

The technical stuff

The 1Password 4 data format uses PBKDF2-HMAC-SHA512 with an absolute minimum of 10,000 iterations when transforming a Master Password to a decryption key. I’m not going to explain what all of that means, but I will say that PBKDF2 is a Password Based Key Derivation Function that is designed to require that there be lots of computation in getting from an entered password to a key. It is specifically designed to slow down cracking attempts.

The attacker is able to build special machines for their cracking efforts, and software carefully optimized for that hardware. Defenders like us have to be able to process a single password in an acceptable amount of time for them on the hardware in their pockets. As a consequence, the attacker can process a candidate password much more quickly than the legitimate user. @bitwiesil, the developer of Cryptohaze, describes this as an Attacker/Defender Ratio (ADR).

For example: if it takes 1/4 of a second for a user’s Master Password to be processed on their mobile device, but the attacker using specialize hardware can make 10,000 guesses per second, the ADR would be 2,500. In a perfect world, the ADR should be 1:1, but that is never going to happen. Plus, ADR in the tens of thousands, instead of in the millions or billions, is a hard but more realistic goal.

The limits of PBKDF2

PBKDF2 isn’t perfect. Most importantly, it can only go so far. We can reach a point where even tiny improvements to a password (say, just adding a digit) can offer far more additional protection than adding extra strength to PBKDF2. For example, adding a single random digit to the end of a password will offer as much as going from 30,000 PBKDF2 iterations to 300,000. And the latter can do real harm in making legitimate decryption too slow. Increasing the number of PBKDF2 iterations does not change the Attacker/Defender ratio at all.

There are a couple of other things that PBKDF2 doesn’t do. When it uses SHA1 internally (a very common configuration), it can be optimized to run extremely quickly in GPUs, giving the attacker a high ADR. Computers built with several (or many) GPUs operating in parallel can still perform many billions of SHA1 computation per second. GPUs cannot be so easily tuned when PBKDF2 uses SHA512 instead of SHA1. Our use of SHA512 within PBKDF2 in 1Password 4 is overwhelmingly the biggest reason that we are seeing such a small Attacker Defender Ratio in the hashcat report.

There is another, more subtle issue with PBKDF2 which can allow the attacker to double the ADR in some peculiar cases. Those cases can be avoided (once people know to avoid them), and a doubling of the ADR is not a big deal. But this does show that PBKDF2 is not the slow hash we would design today.

PBKDF2 is not “memory hard”. It is designed to raise the cost in computation for both attacker and defender, but it doesn’t force a substantial demand on computer memory. If, as the case has been, that the price of computations falls faster than the price of computer memory, the attacker can affordably purchase or rent a fleet of fast processors. But, if we build a slow hash function that also requires substantial memory use, we have more flexibility in trying to reduce the ADR.

So why do we stick with PBKDF2?

For all of its warts, PBKDF2 is the best choice for 1Password today, although it may not be tomorrow.  We can mitigate some of the limitations of PBKDF2 in our design, which we currently do. After all, the great results that we have from this weekend’s hashcat report show that we continue to be successful with it.

The best alternative to PBKDF2 that is reasonably well available and scrutinized is scrypt. If scrypt or similar had been further along as a standard, we probably would have used that. But because you need to unlock your 1Password data on a variety of different platforms, we need to use cryptographic functions that are included in well-tested libraries for all of those platforms.

This is why the Password Hashing Competition is so important. This is an effort to develop and agree upon a design for a successor to PBKDF2 that takes into account everything we’ve learned since it was first developed. The aim is that the successor will have enough support to become available to developers in many cryptographic tool kits. But that is a hope for the future. Right now we continue to use PBKDF2 in a way that takes its various quirks into account.

Your part of the job

Even the slowest hash with a perfect Attacker/Defender Ratio can’t protect a weak Master Password. Our job is to make sure that, when an attacker needs to guess trillions of passwords, they have to really work to do so. Your job is to pick a good Master Password so that it is trillions of passwords they need to guess instead of thousands. In our sample data that hashcat used, the password was “fred” (this was also made public). So even performing less than 500 guesses per second, hashcat was able to find the password “fred” in less than a minute.

Updated to correct spelling and add in a few links.

On hashcat and strong Master Passwords as your best protection

HashcatYou may have heard some news going around about hashcat, a password cracking tool, that recently increased its ability to guess Master Passwords for 1Password data files. It’s an impressive achievement for hashcat, and it is important to understand what this does and doesn’t mean for 1Password.

What you need to know

1Password has not been “cracked”

The existence of a new cracking tool (actually there is another new tool, but only the hashcat one is getting much attention due to its speed) does not mean that anything is broken in 1Password. Indeed, the fact that we are open about our design is one of our strengths. Hashcat’s remarkable guessing speeds is the real news here.

Your Master Password is your protection

This development only highlights what we’ve said all along: your Master Password is your defense. You need to pick a strong Master Password, and these are some great posts on how to do that. Our measures to slow down automated guessing helps a great deal, but they are no substitute for a great Master Password.

Is there a flaw? Well, yeah. It’s complicated

The announcement said that some of hashcat’s speed achievements is due to a flaw in the design of the Agile Keychain Format. Indeed, there is a very subtle flaw. Exactly how much the flaw contributes to their cracking speed is something I’ll talk about below. In short, it contributes—literally—one bit.  But more on that later.

There are a couple of technical misunderstandings about the flaw that I’d like mention here in our “cliff notes introduction”, but with the details and explanation to come further below.

  1. We didn’t call PBKDF2 twice during key derivation (that would be silly). However, we called PDBDF2 once in a way that had the effect of calling it twice. That is still a flaw because it has the identical result of doing something silly, but it was a non-silly flaw.
  2. Hashcat was able to reduce the number of hash calls four fold. But our flaw was only half of that. The other half is not specific to 1Password.

Terrific community

Understanding the precise nature of the “flaw” and related issues was a communal effort involving hashcat developers, John the Ripper developers, cryptographers, and members of the information security community. The debate, discussion, questioning, and explaining within this community is fantastic.  Some  the debate continues and not everyone involved will agree with every point of the more detailed assessment below.

More background

Ready for the next level of detail? Here goes.

Password crackers and how to defend against them

John the RipperPassword crackers, such as John the Ripper and hashcat, are tools that automate password guessing. Over the past year, they have turned their attention to password managers, including 1Password. This doesn’t reflect a weakness in password managers in any way. Indeed, I think the fact that we were among the first to draw this sort of attention is to our credit. The question isn’t whether someone has tools to automate password guessing—we should always assume that they do—but how many guesses can be checked in a short period of time. The faster they can guess, the stronger people’s passwords need to be.

Naturally, we have put in measures to make password guessing slow. We use PBKDF2, which requires that there be lots of computations to go from an entered Master Password to actually unlocking your 1Password data. Then the question is about how good a job our use of PBKDF2 does against these highly optimized tools. The short answer is that PBKDF2 helps enormously, but it is no substitute for a strong Master Password. When we get to the technical discussion (if you stick with me that far), you will learn a great deal more about PBKDF2.

What does this mean for my Master Password?

For a couple thousand dollars today, an attacker can build a machine that will guess millions of 1Password Master Passwords per second. So let’s look at how long it would take for that to crack various types of Master Passwords, assuming the scenario of an attacker getting a copy of your Agile Keychain and setting this machine to work on nothing other than guessing your Master Password.

Password strength comparison

hashcat-crack-timesFor the numbers I give, I’m going to pretend that you all created Master Passwords using the scheme in Toward Better Master Passwords, called “diceware.” It’s not because I actually assume that everyone is using that system, but we need to know how strong a password is (measured in bits of entropy) to perform calculations about how long it might take to guess them. It is remarkably hard to know how strong a password is just by counting letters, digits, and symbols. Instead you need to understand the system that was used to create the password.

If you have a three word diceware password with 1Password using 10000 PBKDF2 iterations, the hashcat machine (more on that in a bit) would have a 50% chance of running through all three word-long diceware passwords in about nine days. If you use a four word password then it would take almost 200 years. At five words, it would take 1.5 million years. With six words and above we are talking about billions of years.

What about increasing PBKDF2 iterations?

Password Based Key Derivation Function diagramThe very first versions of the Agile Keychain Format long ago used 1000 PBKDF2 iterations. More recently, when a new keychain is created or the Master Password changed (in version 3.9 for Mac), we changed that to a minimum of 10000 iterations (and possibly more depending on your system). It is tempting to think that we should just increase these numbers dramatically. We will certainly be looking at increasing that minimum, but it is very important to understand that increasing the number of PBKDF2 iterations stops paying off after a while. We reach a point where there is far greater security improvement for the effort making a Master Password stronger than there is for increasing the number of PBKDF2 iterations.

I’m going to talk about the security of Master Passwords in terms of bits of entropy. You don’t need understand the details other than to know that each additional bit doubles the cracking time. So if you have a Master Password that has 40 bits of entropy (basically that there are 2⁴⁰ different alternatives passwords you could have created using the same password creation system) it might take, say, 100 years to crack under certain conditions. If it were one bit more (41 bits) then it would take 200 years to crack under the same circumstance.

We can also double the amount of time to crack by doubling the number of PBKDF2 iterations. Going from 10000 iterations to 20000 doubles the crack time, and so it adds the equivalent of 1 bit to the the effective strength. Going from 1000 PKDF2 iterations to 10000 PBKDF2 iterations (increasing the iterations 10 times) effectively adds about 3.3 bits of entropy. The attacker needs to work 10 times harder. If you go from 10000 iterations to 20000 iterations, you only gain one additional bit. The attacker only needs to work twice as hard. Going from 20000 iterations to 30000 iterations gives about 0.6 bits of additional strength.

Now contrast adding a single randomly chosen lowercase letter to your password. Each one will add 4.7 bits of entropy. That would be like going from 10000 PBKDF2 iterations to 260000 iterations. Adding another randomly chosen lowercase letter would add additional 4.7 bits, but trying to do the same by increasing PBKDF2 iterations would now take us to 6.7 million iterations. Adding a diceware word to your master password will add 13 bits.

To get the same effect as adding a diceware word by adding PBKDF2 iterations would mean going from 10000 PBKDF2 iterations to 78 million iterations. With that, it would probably take more than an hour or two to unlock your 1Password data on an iPhone if the effort didn’t entirely drain the battery first. The simple lesson is that once we have a few tens of thousands of PBKDF2 iterations, increasing them doesn’t add much security, while it does add to real costs to the legitimate user of the data. The more effective route is to spend a second or two typing a longer password instead of having PBKDF2 spend a few seconds exhausting your battery.

Beyond diceware

DiceThe Master Password generation scheme that I recommend in Toward Better Master Passwords involves picking words from a list of 7776 words by rolling dice. We can make these passwords stronger by using a longer list of words. The reason that 7776 is that it works by rolling five dice (or one die five times). We can use a longer word list if we don’t need to roll dice. But it is absolutely essential for the security of the scheme that the process of picking words is really random and not under direct human control.

Another option is to do as I suggested in that article. Create a relatively short password the usual (not very good way), but make sure it isn’t something on the diceware list. Then create a diceware password and simply add the two together.

A third, more complicated option, is something that is a bit of a “work in progress”, but this hashcat news means we can talk about it a little early. The idea is to use lists of words from different languages as well as longer lists of words. Randomly pick which language to use for your first word, then use diceware on that. You may have to learn a few foreign words in the process, but once you’ve learned those words they should be about as easy to remember as the words of your native language.

I have prepared lists of words exactly for this scheme along with a README file that contains not fully fleshed out instructions on how to use the system. This is very experimental, but it has allowed me to have a a strong Master Password for 1Password on iOS which isn’t too annoying to type on an iPhone keyboard or to remember.

The really technical details

I was definitely impressed to learn that they are getting three million trials per second against 1Password data that used 1000 iterations for PBKDF2. It is important to understand how. There were four things that gave them a speed up, and I’ll work from the least (smallest speed up) to the most significant. I should note that some people I have enormous respect for do not fully agree with my assessment. If you’d like to dive into this, please follow the discussion on the hashcat forums.

But first, another word about PBKDF2

Three of the four mechanisms I discuss involve the inner workings of PBKDF2. So we need to peek a bit more into that black box.  PBKDF2 takes something like a password and transforms that password over and over again and eventually spits out a big number (a string of bits). When you call PBKDF2, you not only tell it how many iterations it should run through, but you also tell it what function should be used to transform the data in each round. The function has to be what is called a “pseudo-random function”, but other than that PBKDF2 doesn’t insist on much. We say that PBKDF2 “is constructed” from a PRF.

The PRF that is typically used with PBKDF2 is HMAC. I’ve written about HMAC before. Now HMAC is constructed from a hash function, and a number of different hash functions will work. Different hash functions give different size output. SHA1 gives 20 bytes of output. SHA256 gives 32 bytes, and SHA512 gives 64 bytes of output.  If you call SHA1 but only need 16 bytes of output you just take the first 16 bytes of of the 20 byte output and throw away the rest. This is called “truncating”.

The hash functions we use are constructed from “compression functions”. Compression functions are designed to be fast, but they are still where the real computation takes place. So the idea of PBKDF2 is to require that the underlying compression function is computed many times.

All of these concepts and constructions will play a role in the discussion of points 2, 3, and 4 below. But first, to the one that has nothing to do with PBKDF2.

1. Only one AES block needs be decrypted per guess

When data is encrypted using a block cipher (such as AES) in CBC mode with standard padding, the attacker doesn’t need to decrypt each block of ciphertext to see if things “work”. The attacker only needs to decrypt the final block. This is not anything particularly new, but it is an important optimization. This way, the attacker needs only one AES decryption per guess.

An aside to any application developers: It is perfectly fine for an attacker to use this shortcut, but applications should never, ever, ever, use this trick as a way to report decryption success or failure. Really. Don’t do it.

Again, I believe (but haven’t confirmed) that other crackers running against CBC mode use the same optimization. It’s an optimization, but a typical one and doesn’t represent a flaw. We want the slowdown to take place in PBKDF2.

2. PBKDF2-HMAC optimization

There is a neat trick that can be used to speed up PBKDF2-HMAC calculations by a factor of two. I first saw this trick in John the Ripper, and it is used here in hashcat as well. Now this optimization, however, is available to defenders as well as to attackers. So if our use of PBKDF2 uses the same trick as is used in hashcat and John the Ripper then this comes out as a tie between Attacker (them) and Defender (us).

HMAC diagramPBKDF2 calls HMAC for each iteration. Each run of HMAC normally involves two hashing operations. Each of those two hashing operations involve two compressions. So we have four compressions altogether for each call to HMAC. However, two of those compressions are going to be exactly the same (with the same data) for each PBKDF2 iteration. If we compute those two compressions only once and save those results, then we can cut down the computation needed for each PBKDF2 round in half.

This optimization of PBKDF2-HMAC-SHAn is available to both the attacker and to the defender. So this only really counts as a “speed up” for the attacker if the defender isn’t using it and isn’t taking it into account when calibrating the number of PBKDF2 iterations. So does 1Password use this optimization? It depends on the particular software libraries we use. I believe (but haven’t received confirmation from Apple on this yet) that the PBKDF2 implementation in CommonCrypto does do this. I don’t believe that the cryptographic library we use for 1Password for Windows does, which might help explain why unlocking 1Password on Windows takes a bit longer than it does on the Mac. Indeed, we’ve been looking at using our own custom PBKDF2 implementation on Windows specifically to get this optimization.

3. Don’t ask more of PBKDF2 than it is ready to give

This is where the design flaw in the Agile Keychain key derivation mechanism. We ask PBKDF2 to give us 32 bytes of data, but we also tell it to use HMAC-SHA1. This, combined with the fact that we used one half of its output for one thing and the other half for another, is our misdesign.

SHA1 only produces 20 bytes of data and so if we ask PBKDF2-HMAC-SHA1 for 32 bytes of data it can’t run its natural course. Instead what it does (with some rounding and truncating) is run PBKDF1 (which gives at most 20 bytes of output) twice. Once to produce the first 16 bytes that we asked for and once to produce the second 16 bytes of output. If we asked it 10000 iterations, it will actually run through 20000 iterations, 10000 to produce the first part of the output and 10000 to produce the second part of the output.  This is a fact about PBKDF2 that we were not aware of at the time.

Normally this behavior of PBKDF2 wouldn’t be a problem, as both the attacker and the defender would suffer from an equal slowdown of twice as many calls to the underlying hash function. But, in the words of Mr Monk, here’s the thing. We used the first 16 bytes that output as a derived AES key and the second 16 bytes as an initialization vector. The password guesser only needs the AES key to see if a password works. To actually decrypt the data, the IV is needed as well, but it is possible for the candidate password to be verified with only the AES key.

Splitting the output of PBKDF2 is a perfectly fine thing to do. Asking for more data from PBKDF2 that you’d natively get from the hash you give it should also be fine. After all, that is something that PBKDF2 was designed to handle. But doing both of those turns out to allow an attacker to do just half of the work that you need to do when you run PBKDF2.

Without this flaw, the guess rate would still be 3 million guesses per second for 1000 PBKDF2 iterations. It just means that our own use of PBKDF2 would “cost” half as much and so that we could double the number of iterations.

4. Really, really well designed GPU processing

Radeon hd 6990Hashcat does many things well, but I think that what they really excel at is GPU processing and parallelization. Their ability to spread out all of the work among four GPUs and have each one perform SHA1 computations very quickly is, I believe, where the real speed is.

The compression functions (invoked by the hash functions, invoked by HMAC, invoked by PBKDF2) happen to run really nicely on GPUs, and all of the constructions build on top of them also have nothing in them that presents difficulties for highly optimized code on GPUs. So roughly speaking, PBKDF2 provides no meaningful defense against parallel computation, and its typical components can be implemented very very nicely on GPUs.

Beyond PBKDF2

As we look at the above list, we see that three of them involve design features of PBKDF2. PBKDF2 is not serving its purpose as well as we would want. Now I love PBKDF2. It may not be engraved on my heart, but it is engraved on my iPad.iPad-Engraving But it has been growing clearer that the world needs a successor to PBKDF2. A possible successor, scrypt, does consume memory as well a CPU (or GPU). But PBKDF2, scrypt, and the search for a successor will have to be the topic of a separate article. Indeed, it is the subject of the article that I would have been working on today had not the hashcat announcement come.

We continue to use PBKDF2 in our new data format, but with some important changes. First of all, we use SHA512 which makes it safe for us to ask for 64 bytes of data that we do split into halves. Also our use of SHA512 should make things more difficult for GPU-based crackers. Exactly how difficult remains to be seen.

Our next steps

Quite simply it is far too early to promise specific changes in response to this. Changing the key derivation system in the Agile Keychain isn’t something that can be done quickly, as we would need to make sure that 1Password on every single platform we support would be ready for the change before we started converting data files. I’m not ruling that out; but it would take a great deal of time, be fraught with compatibility issues, and would only save one bit worth of effective password strength.

We could boost the number of PBKDF2 iterations, but as described above, we’ve reached a point of diminishing returns for that. It will probably happen slowly and behind the scenes, as it has done in the past.

We can make certain that all our PBKDF2 implementations perform the HMAC-PBKDF2 optimization. We were already in the process of doing this when the hashcat news broke.

We can advise people on creating stronger Master Passwords, as that has and continues to be your best protection. Indeed, we will continue to do so as we also explore ways to make it easier for people to create and use such passwords.

[Update 1: At the moment, changing your Master Password will only recalibrate the number of PBKDF2 iterations when you use 1Password 3.9 on the Mac. We will have further information about 3.8 and 1Password on other platforms shortly.]

[Update 2:  PBKDF2 settings for different versions of 1Password.

Calibration requires something introduced in OS X 10.7 (Lion) and iOS 5. So calibration is only available in the Mac App Store version of 1Password for Mac (which requires OS X 10.7) and in 1Password 4 for iOS (which requires iOS 6). 1Password for Windows, 1Password for Mac 3.0-8, and 1Password 3 on iOS do not calibrate.

  • 1Password 3.9 Mac: All versions of 1Password for Mac from the Mac App Store (MAS) calibrate the number of PBKDF2 iteration on initial set up and on Master Password change. A minimum of 10000 iterations is used.
  • 1Password 4 iOS: All versions of 1Password 4 for iOS calibrate the number of PBKDF2 iteration on initial set up and on Master Password change. A minimum of 10000 iterations is used.
  • Mac 1Password 2.5.0 (October 2007) – 3.8.10:  Keychains were created using 1000 PBKDF2 iterations.
  • Mac 1Password 3.8.11 (December, 2011) – 3.8.20: Keychains were created using 10000 PBKDF2 iterations. Changing the Master Password did not change iterations.
  • Mac 1Password 3.8.21 (April 2013): Keychains are created using 10000 PBKDF2 iterations. On a Master Password change, iterations will be increased from 1000 to 10000 if necessary.
  • Windows 1Password (April 2010) – 1Password Keychains created with 1000 PBKDF2 iterations.
  • Windows 1Password (October 2012) – 1Password Keychains created with 10000 PBKDF2 iterations.  Master Password change does not increase number of iterations.
  • Windows 1Password (May 2013): Keychains are created using 10000 PBKDF2 iterations. On a Master Password change, iterations will be increased from 1000 to 10000 if necessary.

Please note that that making a small improvement to your Master Password has a far far greater effect than making a large increase in the number of PBKDF2 iterations.]

[Update 3: 1Password and  hashcat: The Movie.

I presented on this at PasswordsCon in Las Vegas on Juny 31, 2013. Per Thorsheim, one of the organizers of the conference, has uploaded videos of the talks.

But really, you would be better off watching the other talks from PasswordsCon. You already know what I have to say. The other talks were fantastic. You can also get the  PDF slides for that presentation.]

1Password is Ready for John the Ripper

John the Ripper, the pre-eminent password cracking tool, is getting ready to take on 1Password. Is 1Password ready? Yes! We have been ready for a long time, but you need to do your part by having a good Master Password.

We’ve written many times about how 1Password defends against automated password guessing programs (password crackers). And we’ve been strengthening those defenses as well. If you’ve been wondering why we’ve been devoting so much effort to this, well this is the article for you.

We’ve always known that that there is nothing we can do prevent someone developing an automated Master Password guessing tool that is tuned to 1Password data, and so we’ve designed our security around the assumption that such tools do exist. What we can do (and have done) is make any password guessing program work extra hard, so that it can only guess thousands of passwords per second instead of many millions per second. We also have been advising people to make sure that their 1Password Master Passwords are strong, unique, and memorable.

What’s new

Password crackers don’t break the cryptography or exploit bugs or design weaknesses. They are just programs that try millions or billions of different passwords until they either find one that works or the person running the program gives up.

John the RipperThe news is that the most popular and sophisticated open source password cracking tools available, John the Ripper, is now being adapted toward cracking password managers Master Passwords. More recently (July 25) we see the development of tools specifically designed for making John the Ripper work with 1Password’s Agile Keychain Format.

John the Ripper expects the data that it works with to be in particular formats. The modifications to John the Ripper for 1Password involve two components. One converts the relevant part of the Agile Keychain Format into an appropriate input file, and the second part allows John the Ripper to test against that input file in a way that allows it to recognize a successful guess.

Let me stress again that the existence of a password cracking tool does not reflect any kind of weakness in the system it is attacking. When you have encrypted data, there is nothing stopping a person or a computer from trying to guess the password.

What’s not new

Other than repeating the fact that 1Password users should have a unique, strong, and memorable Master Password, there is nothing that we need to do with 1Password in response to the new components of John the Ripper. We have been operating under the assumption that these sorts of tools already existed, even if they hadn’t been made publicly available.

PBKDF2 diagramWhen we introduced the 1Password data format in 2008, we knew that we needed to design it to defend against crackers, so we used PBKDF2 in the process of getting from Master Password to encryption key. PBKDF2 means that a computer has to do many complicated and slow computations to derive an encryption key from a password. So you might have to wait half a second or so after entering your master password for 1Password to actually be able to unlock your data, but that is barely noticeable to someone using the system. But for an automated password cracking system, it dramatically reduces the number of possible passwords it can guess in a day. We’ve written more about how PBKDF2 works in Peanut Butter Keeps Dogs Friendly, too. Plus, last year we increased the number of PBKDF2 iterations that many versions of 1Password use when creating a new data file.

We have also been encouraging people to use good Master Passwords for their 1Password data. 1Password means that your various login passwords don’t need to be anything that you need to remember (and so it is easy for those to be strong and unique), but your 1Password Master Password is something that needs to be strong, unique, easy to remember, and reasonable to type. There is a great deal of advice on the ‘net about how to pick a good password that you can remember, but much of that advice fails to take into account the flexibility of password cracking tools. So please take a look at Toward Better Master Passwords if you haven’t already looked at that.

How fast in John the Ripper and what does it mean for your master password?

I’ve spent much of the weekend playing with the new tools in the developer versions of John the Ripper.CPU cores are completely pegged I ran John the Ripper (JtR) against my 1Password data for about 20 minutes on my Early 2009 Mac Pro (Quad Core). John the Ripper cranked away and consumed more CPU power than I knew my machine had (see picture at right). Yet working against a 1Password data file that used 1000 PBKDF2 iterations, JtR was only able to try about 4200 password guesses per second. For my calculations in the table below, I rounded that up to 5000 guesses per second.

I also tested a data file with 28,000 PBKDF2 iterations. As expected John the Ripper was slowed down about 28 times from the case with 1000 PBKDF2 iterations.  In the table I provide estimated cracking times if the data file uses 25000 PBKDF2 iterations, which should make JtR run about 25 times slower than when there are 1000 iterations. (Again, my timing data was a bit messier, but I am always rounding toward the worst case. That is, whenever there is some ambiguity or a range of results, I am always picking the estimates that would have John the Ripper be faster.)

The author of the 1Password plug-in, Dhiru Kholia, anticipates that the module will soon be modified so that it can make use of Graphic Processor Units (GPUs). This, he estimates, will increase the guessing speed by more than 100 times. In my table below, I have used a 200 times increase in speed for GPUs. So that where I had roughly 5000 guesses per second on my Mac Pro, I assume that with GPU acceleration, there will be one million guesses per second.

Mac Pro (Early 2009)And finally to read the table below, you need to be reminded of how I am measuring password strength. I can only calculate the strength of a password if I know the system by which the password was created. A great deal of advice floating around about creating passwords fails to take into account that the attackers know more about how people create passwords than the people creating the passwords, and these attackers can and do tune their cracking tools accordingly. Much of the common advice also fails to take into account that people are far more predictable than we imagine. So passwords that may look really strong are often far weaker than people imagine.

If you read the advice in Toward Better Master Passwords, you will see that the recommended system is to pick words from a list truly at random (by rolling dice) and then just using that sequence of randomly chosen words as your Master Passwords. This sort of system, until it became the subject of an xkcd comic, was known as diceware.

The table below looks at Master Passwords 3, 4, 5, 6, and 7 diceware words long. The entropy of those passwords are listed in bits. For an explanation of what “bits of entropy” means, take a look at The Geek Edition of the article on better master passwords.

The cracking times are the average or mean time to crack. For example if it would take 116 years to try every possible 4 word password created with the diceware scheme, then it would take on average 58 years.

JtR crack times for agilekeychain


From the table you should surmise that three-word-long passwords of this sort aren’t long enough to withstand a plausible attack. You should also be able to see that anything over five words long is overkill. Or, given a Master Password with more than about 55 bits of real entropy (not the false reports that you get from most websites pretend to calculate password strength), you should be fine against any plausible attack for a long time to come.

PBKDF2 and its limits

It really is because of PBKDF2 that tools like John the Ripper will only be able to find weak Master Passwords. Its role is vital. But it is important to notice that once we have a sufficient number of PBKDF2 iterations, increasing those doesn’t add that much additional security. Going from 1000 iterations to 25000 iterations is the equivalent of adding less than 5 bits of entropy to a password, which is about the same as adding a truly random, lowercase letter to a password. Furthermore, there are continuing diminishing returns: Going from, say, 25,000 PBKDF2 iterations to 50,000 would only add the equivalent of one bit of entropy to a password.

In short, once PBKDF2 is in place with a reasonable number of iterations, you get far far more security for the effort by making your Master Password stronger.

Why doesn’t 1Password limit the number of password attempts?

Many websites or an ATM will lock someone out if they enter their password incorrectly too many times. Websites will also have a kind of back-off. After you’ve entered your password incorrectly three times in a row, it may make you wait ten minutes before it lets you try again. These are very good security measures for those sorts of services. So the question is: why don’t we do the same with unlocking 1Password?

1Password stores your encrypted data on your computer. You may use Dropbox for syncing, but when 1Password does its thing, it is always unlocking data that is on your computer. This means that if an attacker gets hold of your 1Password data (say your computer is stolen), they have the data right there. They do not need to use the 1Password software, they can go directly to the data with their own tools. Because an attacker doesn’t have to go through our software or systems we control, there is no place for using using throttling or back-off techniques. We have to build the security into the data format itself. Our use of PBKDF2 is an example of that.

More abstractly and to introduce a bit of technical jargon, your Master Password is an encryption password, not an authentication password. It is used as (or to derive) a key that decrypts something. It is not used as a mechanism to prove who you are so that you could be let into some service. The distinction is subtle, and particularly prone to confusion because, for the most part, a user shouldn’t have to know or care about it. But there are a couple of places where the distinction matters. It is part of the explanation for why 1Password doesn’t do back-off or throttling.

There is one other place that the distinction between encryption password and authentication password matters for users of 1Password. I will be writing about it more later, but in summary: it means that once you have a good 1Password Master Password, you should keep it for life. You gain no security by changing an encryption password frequently (indeed, it can hurt). So you should only change your 1Password Master Password if there is something wrong with your current one. I’ll talk more about changing passwords (when you should and when you shouldn’t) in a future article.

Should we keep our data format secret?

It’s natural to ask whether we could have made things harder for the developers of password cracking tools if we weren’t as open as we are about the design of our data format. We certainly could have made things a bit more annoying for them if we attempted to conceal details of our data format, but we couldn’t have made things harder for them in a way that would have mattered for security.

On the whole, people should be distrustful of systems that claim to gain security by having secrets known only to the developer. That approach is often called security through obscurity. It not only rarely works, but it often implies a weakness in the design. For example, if there were something that I knew about the design of 1Password that would enable me to unlock your data, then it would necessarily be the case that there is a weakness in the system. Such secrets can often be discovered by careful analysis or through the secret actually getting out from those who know it. Despite what I may have said on April Fool’s Day, proprietary encryption systems are a warning sign, not a virtue.

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