Security

How to get people to use strong passwords

Can passwords be both secure and easy to use? Some think "no", but if you stop there, you simply aren't thinking enough.

As noted in "Don't be fooled by the argument against unique passwords," people giving bad security advice claiming that good security practices are impractical and should be ignored seem to be a surprisingly common sight. As the world's security issues become more prevalent and problematic, the rate of such incredibly bad advice being offered seems to increase, and can do increasing amounts of damage where people buy into their message.

An example from 2007 that I have only just encountered is "The Usability of Passwords," which begins:

Security companies and IT people constantly tells us that we should use complex and difficult passwords. This is bad advice, because you can actually make usable, easy to remember and highly secure passwords. In fact, usable passwords are often far better than complex ones.

The underlying assumptions of this statement are several, and almost invariably wrong. First, it suggests that password strength through complexity necessarily makes passwords unusable. Second, it suggests that simple passwords can be "strong enough" for almost all purposes. Third, it subtly suggests -- like the majority of such overly facile arguments -- that convenience trumps security all the time.

Finally, it suggests that its author Thomas Baekdal knows more about security than people who actually study its intricacies. While this may or may not be true in and of itself (at least in some cases) with no further evidence than the first paragraph of The Usability of Passwords, the rest of it serves to demolish such a hypothesis when his incomplete understanding of the factors involved in password security is displayed.

Before proceeding, let us demolish his entire argument with a single fact.

Strong passwords are easy to manage

A good password manager solves the problem of password usability quite neatly in at least 98% of cases. In fact, employing a good password manager can actually make password use easier than heeding the simplistic, dangerous advice of most of these advocates for bad password policy. Using one really strong password for all the "important" sites, and one really weak password for all the "unimportant" sites, requires remembering two passwords, where a password manager only requires remembering one; using differing weak passwords everywhere requires remembering many passwords, which does not really make things much more convenient; and using passphrases made up of easy to remember terms in one's native language requires a lot more typing than a single password for a password management application.

Meanwhile, choosing a password manager carefully and configuring the software well can result in a relatively pleasant experience protecting one's security. The software I typically use is pwsafe with a keyboard shortcut driven interface for the X Window System -- secure, simple, well-designed, and thanks to the addition of my keyboard-driven interface wrapper, it is also very easy to use.

For those using Microsoft's flagship OS, another earlier article covered how to use Password Safe on Microsoft Windows 7. In discussion following both this article and the article discussing how to set up a keyboard driven interface for pwsafe, other suggestions of password manager applications were offered.

The incomplete arguments

Much of the problem with non-secure security arguments like Thomas Baekdal's is an incomplete understanding of how things actually work. Examples drawn from "The Usability of Passwords" are numerous, easily deconstructed, and easily refuted by a more thoughtful individual than its author. Each of them starts with a seed of truth, and proceeds to wander outside the realm of applicability and accuracy when he starts filling in the holes in his understanding with poorly considered conjecture.

How to crack a password

In The Usability of Passwords, its author explains how passwords are cracked (showing his intimate knowledge of the subject by misusing the term "hack" where "crack" would be correct). He lists five possibilities:

  1. Asking
  2. Guessing
  3. Brute Force Attacks
  4. Common Word Attacks
  5. Dictionary Attacks

He (incorrectly, I believe) claims that the most common methods of cracking a password are asking and guessing. While it is true that people asking others for their passwords is probably the most common way that someone might gain access to another's password, the vast majority of these cases involve honest people who intend no harm and are simply trying to get their work done -- or, in some cases, even trying to help the person whose password they acquire in this manner. As for guessing, it boggles the mind to consider the notion that in this age of profitable, computer powered, automated security compromises someone would think that a security cracker sitting down in front of someone's computer and typing in strings of characters to try to gain access to password protected resources lands within the top ten approaches to cracking password security. Do not let CSI: New York fool you into thinking that is a common approach, relative to other approaches Thomas Baekdal listed.

The closest we might get to truly common usage of the "guessing" approach he describes -- using information about an individual to inform one's attempts to guess -- is using information about an individual to prioritize the potential password combinations used in a brute force attack.

The most sophisticated attacks that actually rely on coming up with the password itself are, in some respects, all brute force attacks. What he terms a "common word attack" is in fact a dictionary attack using a "dictionary" smaller than the Oxford English Dictionary. A dictionary attack is just a way to prioritize a brute force attack so that the most likely passwords to be used by security-unconscious users are tried first (or perhaps only). Contrary to his description, in fact, most automated dictionary attacks start with "love", "god", "password", and several other common terms first, rather than just going through the OED in alphabetical order. If the way he described things was accurate, picking "zen" as your password would improve security substantially, while "aardwolf" would mean almost instant compromise (beaten only by "aardvark", proper names, and initialisms like AAPSS). In the real world, "password" comes before either of those options in the vast majority of cases.

How to protect yourself

Following the rhetorical question, "When is a password secure?" we are treated to some dubious claims. For instance, the first claim made:

You cannot protect against "asking" and "guessing", but you can protect yourself from the other forms of attacks.

Well beyond dubious, this is quite blatantly false. To protect yourself from "asking":

Never tell anyone else your password.

As for protecting yourself from "guessing", Thomas Baekdal himself provided the answer to this problem when he first brought it up:

This is the second most common method to access a person's account. It turns out that most people choose a password that is easy to remember, and the easiest ones are those that are related to you as a person. Passwords like: your last name, your wife's name, the name of your cat, the date of birth, your favorite flower etc. are all pretty common. This problem can only be solved by choosing a password with no relation to you as a person.

The next dubious claim immediately follows:

A hacker will usually create an automated script or a program that does the work for him. He isn't going to sit around manually trying 500,000 different words to see if one of them is your password.

The measure of security must then be "how many password requests can the automated program make - e.g. per second". The actual number varies, but most web applications would not be capable of handling more than 100 sign-in requests per second.

It is true that a security cracker is likely to use an automated process to crack a password rather than typing everything by hand (and here he contradicts his own earlier statements about "asking" and "guessing" being the most common). It is also true that the amount of time it takes to try out enough passwords to successfully select the needed password is effectively the measure of password strength.

This claim implies that his rule of no more than 100 password tries per second is invariant and reliable, however. It is not. While 100 per second may be optimistic on the security cracker's part if his script tries to actually sign in via a Web form provided by a server somewhere out there on the Internet, this is far from the only way to crack a password. In fact, most cases of cracking large numbers of passwords involve someone gaining access to a database of encrypted or plaintext passwords, password hashes, or other server-side login data that allows an offline attack. Utilizing technologies like GPU password cracking frameworks and SSD storage of password hash databases for faster access times, fourteen character passwords have been cracked in around five seconds -- much more quickly than the three minutes Thomas Baekdal asserts it would take to crack the password "sun" using a brute force attack. The difference is that in the real world, security crackers are often not so naive as to try to brute force a password via a Web login form.

We then encounter the discussion of how difficult a cracking job is "difficult enough". The claim is made that a password that takes ten years to crack (using the limit of 100 requests per second described above) is unlikely to ever be cracked. His words:

10 years - Now we are talking purely theoretical.

Even if we choose passwords that take ten years to crack at the rates provided by GPU password cracking frameworks in local attacks with SSD storage for the password hash database, this is not "purely theoretical". It is actually quite predictably going to take much less time than ten years to crack such a password at some point in the future -- possibly as soon as tomorrow, if someone comes up with yet another clever trick to speed up the cracking process. With that in mind, this statement of his becomes so naive as to be laughable:

I want a password that takes 1,000 years to crack- let's call this "secure forever".

Maybe, instead of "forever", it can be cracked in an afternoon when someone invents a new approach to password cracking six months from now. Worse yet, the rate of technological advancement is accelerating exponentially.

The answer to our prayers is "NO"

After a set of contrived examples of various passwords and their strengths, Thomas Baekdal has set us up for the Big Reveal. The result:

this is fun

He claims this password -- actually three distinct, short, common words separated by spaces -- takes about 2.5K years to crack. In truth, it takes far less time than that using the GPU cracking methods already mentioned, because it is basically just an eleven word password selected from a set of only 27 possible characters (26 lower case letters and the space character). All he has done is reinvent the concept of the "passphrase", poorly.

Passphrases, loudly touted by many as The Most Secure Thing EVAR, do not in fact increase both convenience and security the way people seem to think. All they do is rearrange the math used to determine how easily a password is cracked.

Tell me -- which do you think is more difficult to crack?

  • this is fun
  • &n" <` O C[

If I was a betting man, I would not put my money on "this is fun". It should be immediately obvious that the first is easier just for the simple fact that this is fun makes use of a set of characters represented by 27 keys on your keyboard with no modifiers (the Shift key, for instance), while &n" <` O C[ makes use of a set of 86 characters used by a random password generator. To give you an idea of how much of a difference this makes, Thomas Baekdal's example offers 5,559,060,566,555,523 different possibilities from his implied character set, or over five quadrillion. My eleven character password offers 1,903,193,578,437,064,103,936 different possibilities, or almost two sextillion -- almost 20,000,000 (twenty million) times as many possibilities. It gets even better if I want a longer password, because adding just one more character multiplies the number of possibilities by 86.

For anything nontrivial, though, I do not trust an eleven character password, using a character set of 86. Twenty is a reasonably good minimum number of characters today, for only moderately important cases. With a good password manager, I can use fifty character passwords if I want to -- as long as the login system allows them -- and do it much more easily than remembering a different equivalent to "this is fun" for each such case. After a while, anyone might forget which site uses "this is fun" and which uses "my alsatian spot".

That, of course, completely ignores an even bigger problem with passphrases like "this is fun". Sure, it is an eleven character password with spaces in it, but that is not all it is. It is also a non-random eleven character password. Given that all the words involved are common words, we now face the problem of using a passphrase having done nothing more profound than moving the goalposts a little. Once the kicker gets lined up, aiming is not so much more difficult than it was before the goalposts moved.

From a certain perspective, "this is fun" is just a password with three "characters" in it. The difference is that the "characters" used are taken from a larger character set. A commonly used password cracking wordlist -- the Openwall wordlist collection -- has four million entries in it, but the majority of these can be omitted when performing an initial cracking attempt against an English-speaking user so naive as to use something like "do the dishes" on Thomas Baekdal's advice. The much shorter, public domain list Openwall offers as a free download contains only 3,158 entries. That is a mere 31,494,620,312 possibilities, or about 31.5 billion. Throw in a few articles, particles, and participles, and you are still well under 4K words.

If your security cracker is the least bit sophisticated, the script used to crack passphrases will choose words by parts of speech to fit common patterns. Suddenly, 31.5 billion options will become something much more modest. If the cracking script assumes any two words from the unaltered Openwall list, with one of "is", "was", "can", "cannot", "for", "will", "should", "looks", or "seems" between them, your number of possibilities drops from 31.5 billion to a mere 89,756,676, or under 90 million, less than one third of one percent the number of options.

. . . and we are still including non-random, non-word strings of characters such as "2kids", "1022", and "!@#$%^" amongst the "words" that might be used. Really, to use examples of Thomas Baekdal's system for creating passwords, we should exclude a lot of those -- and end up with something on the order of only 2,500 words. That brings our hypothetical password cracking script's first pass through possible passphrases down to fewer than seven million possibilities. Even at a rate of one hundred tries per second, already discarded as naive when someone might have access to a database of password hashes, we are now looking at a maximum time to crack "this is fun" under twenty hours.

That is much less time than the 2,537 years he claims, and I am not even trying that hard.

Catching up with today

Somewhere along the line, someone must have told him about the flaws in his reasoning, because he offered this defense:

You need direct access to the database file or the server to hack something faster. If you got that level of access, you do not actually need the password. You can just look up the data directly.

This ignores a number of factors, including (but not limited to):

  • The password hash database might be more accessible than other data; authentication might be performed on a separate server from financial data.
  • The user, following the advice of a non-expert like Thomas Baekdal, might use one password everywhere -- thus making a weak password a vulnerability for many other sites.
  • As demonstrated, a less naive approach to password cracking than he imagined might actually work within a single day even under his unlikely constraints.
  • Password databases on stolen smartphones and laptops could provide password hashes without providing any other data from the server the password might be used to access.
  • A flaw in the authentication application could conceivably expose the server to unforeseen work-arounds, and the strength of your password might be the only mitigation.

Other problems may come to mind with more thought. Of course, he takes the defensive measure of trying to exclude offline attacks from his analysis:

What I am talking about in the article is hacking into remote systems (like web apps).

The problem is that the world does not conform to our wishes. Assuming that our passwords are immune to offline attacks just because he decided to ignore them in his Weblog entry is yet another incredibly naive part of his perspective.

Simply pushing away the potential problem of server-side issues that may undermine his argument, such as telling us that passwords are easier to crack if the server admins do not add punitive delays when incorrect passwords are submitted, does not in any way make it less of a problem. The fact of the matter is that people implement crappy authentication systems all the time, and sometimes we use those system -- often without even knowing how badly they were implemented on the back end. Choosing passwords that take longer to crack is a way to mitigate the danger of such poorly designed systems. Saying "it's not my problem" when someone mentions that the server might not be set up to look after your security is nothing more than a good way to provide excuses for not caring about your security.

Yes, the server admin should set up a secure system. No, recognizing that fact does not mean you should not worry about it, even if you are not the server admin.

How I learned to stop worrying and love the password

The real reason people hate strong passwords so much is probably that they are being told to use them by people who, while they are a bit smarter about the difficulty of cracking passwords than Thomas Baekdal, are sometimes downright stupid about security policy enforcement. Telling people they should use long passwords containing capital and lower case letters, numbers, spaces, and special characters just makes the technically uninclined sigh and complain. In "The Usability of Passwords - FAQ," Thomas Baekdal's 2011 follow-up to "The Usability of Passwords," he actually addresses this problem when he discusses why he wrote the original Weblog entry:

The article came to life after yet another discussion with IT, who believed that everyone should be forced to use password with a minimum of eight characters, including two uppercase characters, numbers and a least one special character.

I was absolutely furious for several reasons. First, I knew it was like kicking every employee in the groin every morning they showed up for work, that it would do squat for actual security (it is likely to make it worse), and that it would completely destroy the plans I had for password free web application I was working on at the time.

If I had to type in a password like >9Llz]HX2x8w.5&Go{$k~5pIz&{ every day when I checked my email, another like Rk~b$icSNGz:+1C8`Vp <-~q@un6O to check my bank balance, something like gjj-~ixnCs3{/7yS]r(BW#S,q1?9 to log in at TechRepublic, and many more for every site on the Web, I would hate strong passwords too.

I type exactly one password for everything on the Web, though. I do not use the same password at every site; I just use a password manager, and let that remember all those different passwords of mine.

The key to getting people to stop worrying and love the password is to stop telling people first and foremost to use strong passwords for everything. Yes, they should use strong passwords -- but they should let the password manager handle it for them. Tell them instead to use a password manager, and to configure it to use strong passwords on their behalf.

For more than 98% of cases, your problem is solved by a password manager, and you should not end up being that guy who posts a lengthy explanation of how little he actually understands about passwords and security, thinly disguised as bad advice that a lot of people might actually follow.

About

Chad Perrin is an IT consultant, developer, and freelance professional writer. He holds both Microsoft and CompTIA certifications and is a graduate of two IT industry trade schools.

64 comments
Neon Samurai
Neon Samurai

I'm a big supporter of good password managers also (Keepass for all your Windows,Linux,BSD?,osX,PalmOS,WinCE needs). I run into one problem with them though: The password is in the password manager which must be run on a system. The user must be logged into the system to run the password manager. The result is a login password which must be remembered in order to then enter the manager's unlocking password and access all the strong passwords within. If budgets are not an issue then the solution is multi-factor authentication which does not include a password; at least to get the initial login. In most cases though, we're suggesting use of a password manager when the primary target is the user's system account. Not that I'm going to stop suggesting password managers but it is a conundrum of sorts. (Interesting timing. I've been doing the quarterly password audit over the last week to confirm new LDAP settings and password policy effectiveness.)

Neon Samurai
Neon Samurai

"and that it would completely destroy the plans I had for password free web application I was working on at the time" Interesting factoid that. So the main point of contention was that an improved password policy would conflict with the developer's current designs for an inherently insecure system.

dhays
dhays

The main problem is that some places can have ONLY 8 characters, some up to 250 (like a Windows login), some can only be numbers, some use a subset of characters on a keyboard, some do not allow spaces or slashes for instance, some cannot start with a number, or end with a number, some cannot have repeating characters, some allow anything. The non repeating or no white space password make it difficult to use things like cities and their states with a date and special characters, Changing your password every 90 days or 180 days and no repeats for a set number of passwords (different for each site/application) makes it difficult. Sure I have a printed copy of my passwords, it is normally locked up, but if someone were determined, it is accessible, it is in a matrix format, but someone could figure it out if they wanted to badly enough. They are kept in a password protected file on my computer, again accessible to those who might want to work hard enough. That is my pw manager. I have never used a dedicated one, don't know how they work. I remember my network login, my email login, a couple or more applications, and my pw file password, the rest I have to look up, or it is not a secure password--"Wheel Of Fortune" for instance does not have a secure password. That is not a site I worry about being compromised on. In other words if ALL places at work on around the world had the same rules for passwords life would be easier. I could put a stronger password of similar makeup on all my locations. What I don't like is places that force (not user changeable) you to use your name and a portion of your SSAN as a login name. Of course at home, there is no login to the computer, but it is turned off for days at a time, so it is harder to compromise. I have some external drives that are only occasionally connected, so they are some safer in that respect as they aren't available but a few days a month, if that often. No passwords on my keyboard or monitor, though. Some internet sites that are rarely accessed the password is years old, if the site hasn't dropped me for not accessing them in a certain amount of time. Here is an example from one application I have to use regularly: At least 8 Characters, no white space, no &, -, / Should have at least eight characters. May not contain user's account name. Must contain characters from three of the following types: English upper-case characters English lower-case characters Numerical digits Non-alphanumeric characters Characters cannot be repeated more than once in succession. Minimum lifespan for passwords is two days. Maximum lifespan for passwords is 90 days. A password used in the last 5 cycles cannot be used So my current Lotus Notes Password woud not work, as it has repeating characters and whitespace in its password. Anoter example is: 8 to 15 characters with no character repeated in succession and include at least 1 special character. 1 alpha character. 2 numeric characters Here the limit to the password is fifteen characters, I have several that are more, so are unseable for this application. My Lotus Notes internal and external access have the folowing rules: 1. Must differ from last 50 passwords 2. Use upper and lower case letters, numbersand special characters Changing every 90 days and can't reuse any of the last 50 makes for a long list of passwords and constant discarding of some. That is why I use a simple PW manager (list). It would be impossible to keep up with all 245 sites/applications with passwords (77 total -11 not in use, 59 with less than 5 usage points)

Baphom8
Baphom8

Where I work, we are required to use lengthy complicated non-sensical passwords that change at regualr intervals. Most people have a small notebook somewhere in there desk where the current passwords are maintained.

n4aof
n4aof

Trust all your system access to ONE PASSWORD?!?!?! The notion that using a Password Manager solves all the problems inherent in using multiple complex passwords is even more foolish than the advice to use easy passwords. Using a password manager makes all your passwords vulnerable to a single crack. Oh yes, the argument is that you can keep the password manager on something that isn't connected to any network and therefore supposedly isn't subject to any sort of attack. But that argument falls in the face of reality that most people do not have any unconnected device.

Harry.Hiles
Harry.Hiles

...are the best solution right now. One strong password that you can remember is by far better than using weak passwords and easier than remembering many strong passwords. Choosing a good password manager is important. It must use strong encryption to protect your stored passwords, whether on your laptop or a USB drive. It should also include a random password generator and auto-fill the login fields to make it really simple to use.

seanferd
seanferd

Simple Arithmetic for Faster, More Secure Websites Of course, the original paper is behind a paywall...

Spitfire_Sysop
Spitfire_Sysop

I agree with most of your points here but I am weary of a Password Manager as a solution. If everyone used a password manager then it would make sense for all crackers of the world to concentrate their focus upon the manager application itself. If one person knew about one weakness in the password manager software they would have access to every site for every person running that application. It is a solution that becomes a new attack vector itself. The other problem I see is being without your password manager. If you wanted to access your accounts from a different computer you would need a copy of this program on you and it would have to be synced with whatever computer you last made a change from. Now you have all of your passwords on a thumb drive and it's kinda like carrying all of your passwords written on a paper in your wallet. Sure, the manager database from the thumb drive would have to be cracked but we are talking about offline attacks here. How secure is this "password safe" and how long would it take for it to give up it's secrets if you put it up agenst the same GPU cracker with SSD hard drive? Honest question. I would really like to know.

Neon Samurai
Neon Samurai

Might not get PII about you but they can infect the system and capture the information that is transient though not stored next time your on. They can also abuse the system resources and mis-represent you in the process. It's not simply a matter of "I don't have anything written down so I don't have to protect the notepad".

Harry.Hiles
Harry.Hiles

LastPass is a browser based PM that has a multi-factor authentication option using a a USB thumb drive or a YubiKey. You still need to use the standard credentials (ID/password) along with the USB drive, but it's more secure than just using your standard credentials.

apotheon
apotheon

I found that a bit silly, too.

apotheon
apotheon

> The main problem is that some places can have ONLY 8 characters That is certainly a problem. As I said in Fight Back Against Bad Password Policy, policies that artificially limit one's password options in ways that weaken them are bad, and should be opposed. The same goes for PINs as passwords, disallowing special characters, and so on. > In other words if ALL places at work on around the world had the same rules for passwords life would be easier. A good password manger can solve that problem for you. > What I don't like is places that force (not user changeable) you to use your name and a portion of your SSAN as a login name. My "significant other" has to work somewhere that does stupid crap like that, and she was appalled at the inadvisability of that policy. That sort of thing is beyond stupid. > That is why I use a simple PW manager (list). It would be impossible to keep up with all 245 sites/applications with passwords (77 total -11 not in use, 59 with less than 5 usage points) For a while, I used an OpenPGP-encrypted file as my password manager, with some helper scripts (including one that generated random strong passwords for me when I needed a new password), but pwsafe on FreeBSD has proved far superior to the encrypted file approach -- even with the helper scripts I wrote. I still plan to write my own password manager at some point. As much as pwsafe has proven useful for me, it's not perfect for my preferences. That's true of most of the software in my life, though, so the list of things I'd like to recreate is getting pretty long.

apotheon
apotheon

That's an argument for password managers. I'll try this one more time: Use a password manager. Problem solved.

Michael Jay
Michael Jay

on a sticky note under the keyboard. Or, yikes, right on the monitor bezel.

Neon Samurai
Neon Samurai

Use a password manager that allows certificate authentication instead of password authentication or choose a good strong passphrase if your going to rely on a password to open your manager's database. Either of these remains far better than multiple weak and memorable passwords. Don't shoot down the password manager suggestion just because you don't understand it and/or unless you can provide a better recommendation.

Harry.Hiles
Harry.Hiles

Using a PM is not more foolish than using easy passwords. Attacking a PM requires a hacker to penetrate more security layers than attacking a publicly accessible web site. While it's possible a hacker might be able to convince some people to download malware to their PC and attack their PM, there are other defenses that can prevent this type of attack. The most obvious of these is to recognize the phishing attack and not download anything to your PC that you don't absolutely trust. Plus, web browsers' anti-phishing defenses are getting better all the time. Although imperfect at best, a good PM provides a workable solution for replacing simple common passwords with unique complex passwords, which reduces the risk of someone hacking into your password protected sites. Until a better security solution becomes practical that emphasizes the "what you are" or "what you have" authentication factors rather than just the "what your know" factor, a good PM is the best solution for now.

apotheon
apotheon

> Using a password manager makes all your passwords vulnerable to a single crack. So does using MS Windows. So does using the same password for everything. If you use passwords that are all very, very easy to crack, nobody needs a single crack for all your passwords; malicious security crackers can just crack each of your passwords at the time they're needed. A password manager on an OS that isn't easily compromised is about as secure as it gets right now for dealing with the need for dozens of passwords. > Oh yes, the argument is that you can keep the password manager on something that isn't connected to any network and therefore supposedly isn't subject to any sort of attack. That's a piss-poor argument, actually. Yours, unfortunately, is worse. You seriously seem to believe that using your birthday or your dog's name for everything is better than using a password manager with a strong password protecting dozens of separate strong passwords. That boggles my mind. That, or you think everyone in the world should just have 150 different strong passwords memorized, which is more security if you can pull it off -- but if so, you're pretty much the only one.

steve
steve

My various banking sites all have differing ways of preventing me from using a password manager to enter data in them. One requires me to use a randomized on-screen key pad to enter only numbers. Another has an on-screen keyboard that randomly moves around the screen as keys are entered. A third won't accept automated input into the password field, or even a paste. All laudable ways of preventing morons from giving out the keys to the kingdom, but frustrating for those of us who take this stuff seriously.

apotheon
apotheon

The explanation is not complete enough to really get a handle on how it works. It sounds promising, though, if all the claims about it are accurate with no hidden gotchas or restrictions on use case.

Neon Samurai
Neon Samurai

The password manager can be configured to provide good passwords so that releases the user from the issue. The choice becomes picking a good password manager. I'm sure it's been mentioned already as this is a stale discussion I'm arriving to late but.. - open source solutions; the people who write them are as motivated to maintain privacy as you are when using it. If it is open source, the developer has far more motivation to make it a secure solution than they do to include malicious intent or poor programming habits. If it's closed source, well.. why when there are open source managers readily available. After all, this is very closely related to cryptography; an area where solutions are only ever trusted and accepted through transparent design and rigorous peer review. So, we can trust the manager itself but what of the database it stores your secrets inside? - look for how the password database is stored. I'm looking at a password database encrypted with AES 256bit. Good luck with breaking that and when it becomes breakable through cryptanalysis, the manager's developers will be offering 512 bit aes or whatever the next trusted algorithm from cryptographers is. So, we can trust the database the passwords are stored in. You can't break my manager and you can't take the database to break it separately in your lab. But how is that opened then? - consider the manager's access methods. I'm looking at a password database unlocked by passphrase, by certificate or by user login. I wouldn't trust user login simply because single sign on is a bad idea all around when your users are limited to a memorable login password before gaining access to the password manager full of strong strings. Passphrase depends on the user's selection. Remember one complex password which gains you access to your hord of passwords. I like it though it does rely on the user choosing a good first password. Certificates are a more interesting aproach. You don't want the certificate on the same device as the password manager obviously and having the password manager on the computer is less than ideal given the ease of keeping the password database on secure removable media. Your user may be looking at having two removable devices but if it's justified; why not. For a slick setup, you can consider hosting your password manager on an Ironkey. We've got the encrypted database accessed by passphrase/certificate through open source software. Now add the crunchy outer shell; ten incorrect guesses and the ironkey burns itself, tamper with it and the ironkey burns itself, do not store the recovery password on Ironkey's value-add website and you remove third party targets. If your really paranoid and going the password manager with certificate rough; put your access certificate on a second ironkey. Your still only remembering two strong passphrases with a first layer of defense very unforgiving of wrong guesses. As a single point of failure, a password manager's risks can be mitigated out of existence considering that Ironkey was developed initially for military use and is one of the few products that's withstood third party security researcher auditing to the point that the researcher now uses Ironkeys for personal and client data.

gavin142
gavin142

storing my encrypted password manager database on an IRONKey hardware encrypted USB drive. Before they can try cracking my database, first, they have to crack into the drive itself. So yes, I have to remember more than 1 strong password, but 2 ain't so hard to do :)

apotheon
apotheon

By the way . . . > I agree with most of your points here but I am weary of a Password Manager as a solution. I think the word you want here is "wary", and not "weary".

apotheon
apotheon

You're referring to the "monoculture" problem. The monoculture problem is widely misunderstood and misapplied. Even if it turns out to become a problem for password managers at some point in the future when 70% of homo onlinicus uses them, and even if for some reason people all use similar enough password managers for the monoculture problem to apply, we are nowhere near that day. 1. Even if there's a weakness in a given password manager, a malicious security cracker would need to get to the password manager to take advantage of it. Don't use a password manager that's accessible over the Internet, and keep your computer compromise free. If you can't keep the computer compromise free, you have problems that a password manager cannot make worse. 2. If you want to carry your password manager around with you, do so. Put a password manager, or at least its database, on a USB flash media storage device. Voila. A good password manager will keep the database encrypted, and the "paper in your wallet" problem thus does not apply. The only problem is if you are so careless as to let it leave your possession. 3. The likelihood of a conscientious person losing control of passwords on a USB flash media storage device are much lower than of such a person's one-password-for-everything to get compromised. Seriously. Don't reject the "better" option because it's not "perfect". 4. I, for one, do not need all my passwords with me all the time, anyway. I keep them on a secured computer, and I keep a backup. I do not carry them around with me, because frankly I should not be using those passwords from just any damned computer I do not control, anyway. 5. I'll make a deal with you. If you use a password manager to enhance the security of your computing life until such time as the monoculture problem rears its ugly head (by which time we'll probably have a better solution than password managers anyway, and I'll have recommended moving to that), I won't complain if you stop using password managers when the monoculture problem becomes a reality for password managers. 'Cause, y'know, it's not a problem now, and it won't be for a while at least -- if ever.

Neon Samurai
Neon Samurai

keepass can use a certificate though you wouldn't want it on the same media as the keepass database it unlocks. I was thinking more for the initial login. If you can't log onto a computer, you can't open your password manager so storing your initial login credentials becomes less helpful. it's a chicken and egg problem unless one springs for multi-factor authenticated login. The problem is that removing the password (something you know) leaves you with something you have and something you are.. so.. a certificate dongle and your removed thumb or eyeball if someone is really that motivated. I'll give up my password long before I'll give up body parts; thankfully, I really don't have anything that important to motivate an attacker.

apotheon
apotheon

> Don't shoot down the password manager suggestion just because you don't understand it and/or unless you can provide a better recommendation. That's really the crux of the matter. We are tool-using humans, after all. We should use tools -- not be tools.

apotheon
apotheon

> While it's possible a hacker might be able to convince some people to download malware to their PC and attack their PM, there are other defenses that can prevent this type of attack. That is true, but there is another factor to consider: regardless of whether you're using a password manager, the game is pretty much over if you end up getting the system where you use your passwords infected, anyway. If you type in all your passwords, for instance, you are susceptible to compromise by a keylogger. If you are using passwords to access a remote system, malware could conceivably skim passwords out of memory. Just don't let your system get compromised. Even if it does get compromised, a password manager at least gives you a centralized list of passwords you will need to change after wiping the system and reinstalling from scratch. > Until a better security solution becomes practical that emphasizes the "what you are" or "what you have" authentication factors rather than just the "what your know" factor, a good PM is the best solution for now. re: the "something you are" authentication factor . . . This has problems, too. Thumbprint scanners on your car doors instead of keyholes . . . ? Yeah, then instead of beating you up and taking your keys, a carjacker might beat you up and saw off your thumb. I'd rather let the guy have the damned car.

Michael Jay
Michael Jay

using a passphrase as the key to a password, makes it memorable but cryptic. Such as an epic event in your life, for example "the quick brown fox jumped over the lazy dogs back 1234567890 times" becomes the password "tqBfjotlDb{AlOt}" Just saying, but I have taken to using this concept for making passwords I can remember with ease but seem to be strong.

Harry.Hiles
Harry.Hiles

I also use sites that block the auto-fill function. In these cases, I either copy/paste the password (if allowed) or just type it in. The PM's usefulness is diminished by these sites, but at least it "remembers" all my passwords.

apotheon
apotheon

It's false security for the security-unconscious, at the expense of undermining real security for the security-conscious. Sounds like your various banking sites suck; I feel for you.

seanferd
seanferd

I really hate reporting on what may be good ideas, innovations, research, etc., with no evidence or data available to back it up. Science, engineering, and paywalls. WTF?

apotheon
apotheon

In the article, the first words of the section "Strong passwords are easy to manage" are "A good password manager", and those words comprise a link to the article Five Features of a Good Password Manager. Within that article, the fifth cited feature is "verifiable design", which makes the same point you did about open source software. In short, the article agrees with your assessment of the desirability of open source software for your password manager. Some other important features are mentioned in the same article; I think it's worth reading (though I may be a touch biased, being the author of said article).

Spitfire_Sysop
Spitfire_Sysop

I'm surprised. Some of these arguments are the kind that you would mock me for using in my own defense. It doesn't have to be a monoculture. What if I decided that all the people whom I want to crack used pwsafe and I focus on that? This is the situation I am addressing. 1. If the password manager is interacting with a web browser or e-mail client to enter passwords I see the potential for IE, for example, to allow access to your file system or memory. I am also concerned with the possibility of someone getting access to your database physically. (See: the paper with your password written on it) 2. "The only problem is if you are so careless as to let it leave your possession." This is the same for paper in your pocket. You could even encrypt the writing on the paper but lets not go there. 3. Agreed. 4. Arent we talking about ALL passwords here? From the top secret to the forum you want to post on? Do they all exist in the same database? Do you have multiple databases for different security levels? (I think you should) Or do you remember an extra password for low security sites? (This is what you are trying to get away from) 5. This is the very same argument that you shot down in your article so I will use your words against you: "Maybe, instead of forever, it can be cracked in an afternoon when someone invents a new approach to password cracking six months from now. Worse yet, the rate of technological advancement is accelerating exponentially." I was hoping for a discussion about the security of pwsafe and not a rant bashing my concern.

apotheon
apotheon

Are you aware that we aren't able to upvote ourselves? I suppose you think I'm somehow engineering a voting conspiracy against you, or something like that. By the way, I'm not talking about targeted advertising when I discuss the lack of immunity that you believe you have against security issues. . . . but I tire of this quixotic crusade to educate people, sometimes. Believe what you like. You can even make bizarre fallacious conspiracy theory attacks against me, if you really want to. Have fun with that. I'll leave you to it.

apotheon
apotheon

In one discussion, I'm being harangued by someone who thinks that trying to protect one's privacy and security against corporate bad actors like Apple, Facebook, and and Sony is an act of insanity that indicates I should just give up all technology and live on the street as a Luddite renunciate. In another discussion, I'm dealing with someone who tells me that he can actually use a computer while remaining impervious to harm by somehow magically segregating his private life from his online life. These are incredible extremes. I feel like the "narrator" in a song -- clowns to the left of me, jokers to the right, here I am stuck in the middle. The fact of the matter is that technology advances, and computer technology in particular is a tremendous force multiplier that helps technology continue to move forward at an accelerating pace. It can make our lives much better, help us accomplish far more, and generally be the most transformative, exciting thing in our lives -- but only if we remain vigilant in our attempts to protect ourselves from bad people who use that technology for nefarious ends. Like any other tool, computers can be used for good or ill; we should be willing, even eager, to use it for good, while we take pains to defend ourselves against those who use it for ill so that such a mechanism of positive change is not twisted to destructive ends of unprecedented power. . . . and somehow, by taking this balanced approach, both of the extremists are essentially accusing me (by implication) of extremism.

apotheon
apotheon

> just claimed that what I do "online" and with my systems doesn't matter That's basically the same thing as claiming perfect (online) security.

Who Am I Really
Who Am I Really

just claimed that what I do "online" and with my systems doesn't matter as it's not that interesting to those who would attempt to use it for padding their wallets and if there is a "compromise" it's a matter of wipe and restore and continue on that email from the Nigerian that has an inheritance he needs deposited in a foreign bank to "ensure" he doesn't lose it to whomever is attempting to take it doesn't interest me I don't worship money or status etc. those email photos of Osama don't interest me either who cares what does yer friend's program do with a Bi or Trans? no program is perfect either, just look at winders and the pre-programmed default decisions it makes ! {cough, hack Autorun cough} with the way I use my systems I just don't see a need for using [b]bewaRbkVEARhjrvekjegklEAb)(*&^%$#EARBVkaRBVEjnahueARBhunGRNBmjvilerl4a[/b] as passwords for my email or winders login

apotheon
apotheon

> there's no way Famous last words. Nothing is perfect. > I don't use Like buttons, (or "Hate" buttons for that matter) You don't have to use them. Their very existence on a page you visit (such as an article at TechRepublic) can serve as a foot in the door. > Flash is held hostage to a minimum triple click for approval . . . and the moment you approve some flash you run the risk of opening yourself up to a Flash vulnerability. If you want to be perfectly protected from Flash vulnerabilities, you need to uninstall it. > and User B can "get away with" a moderate password strategy and even if compromised is not at risk for much of any losses of anything My point is that User B is probably overestimating his safety, just as some jackass saying "I use Ubuntu, so my security is invulnerable, because it's the most secure OS ever and it's impossible to compromise Ubuntu!!!!11!1!!!!1!oneone!" is overestimating his safety. > the most you'd have on User B is maybe their writing style . . . and the ability to do things online under the name of User B, and any information about User B that User B's friends has posted online (possibly with links to thinks like User B's "Who Am I Really" profile at TR), and so on, to say nothing of the potential for exploiting an arbitrary remote code execution vulnerability to install a keylogger on User B's computer via cross-site scripting, a presumed-safe Flash object, a stateful connection persistence bug in the firewall used to protect the system, or some other unexpected avenue the malicious security cracker could leverage to gain access. > but even then I don't write exactly the same on every site > > just the same as I wouldn't use certain language in the presence of the Queen or children that I might use in the Bar or toward a drunken retard trying to bum money or a smoke from me I know a guy who wrote a program that can detect your gender based on word selection, sentence structure, and even typing tempo. I think the technology for correlating writing styles is probably well ahead of what you expect.

apotheon
apotheon

> they'd have to have physical access first . . . Why would they need physical access? You said yourself that you're using MS Windows: > I strip winders of as much of it's own spying as I can Are you aware of how common it is to find remotely exploitable vulnerabilities in MS Windows, and in third-party software that runs on MS Windows? Hell, Adobe Flash goes a year or so at a time without critical arbitrary remote execution vulnerabilities being fixed. Neon Samurai mentioned transient information -- that is, stuff that isn't stored. Who cares if you don't save things, once someone gets some kind of monitoring system installed and hidden by a rootkit? . . . and let's not forget the fact that Facebook Like buttons, Google Analytics monitoring, and other third-party activity on sites all over the Web provide interesting ways for your activities to get correlated by those third parties, along with information about you shared by other people you know.

apotheon
apotheon

> I really don't have anything that important to motivate an attacker. . . . you hope.

apotheon
apotheon

A little bit of research can reveal what others might know about you. If you're going to use things you know as the basis of a password, you really need to use something that only you know, and that someone can't figure out by putting together clues. It is too easy to accidentally make a password too weak. The best way to protect against that, I think, is to make all my passwords "too" strong. Better safe than sorry. Aim for passwords so strong that even if someone uses rubber hose cryptanalysis on you, it won't result in your passwords getting cracked. That's one of the beauties of using randomly generated, highly complex passwords via a password manager: you don't even have to know any of your passwords other than the one password needed to use the password manager. The touch of a few keys on your keyboard can then wipe the encrypted password database if need be. It's much more secure than you're likely to need, which means that even if you grossly misjudge the strength you need for your passwords you'll still probably be safe.

Michael Jay
Michael Jay

But I do not have many passwords, and the pass phrases I use are things only someone who knows me very well would have any knowledge about, I have no worries about folks that know me very well trying to break my passwords.

apotheon
apotheon

1. That might work for the first half-dozen or so passwords, if you're really good. After you start getting into the dozens, though, you're pretty well screwed. I have more than a hundred passwords for things I use semi-regularly. 2. If you use a system like that, it starts getting easy for someone who knows anything about you to make educated guesses at how to predict your passwords. Sure, it might be unlikely -- but it might not be as unlikely as you think, depending on your system, and frankly we're not really qualified to judge the strength of our own password mnemonic device systems.

Neon Samurai
Neon Samurai

Read it when fist posted and have it in my PDF library. As I said though, I was late to the discussion and responding to the initial post questioning how a password manager doesn't simply become a single point of failure or easier target. Hopefully the fellow with the initial post also gave it a read though the two of you apear to have found agreement in the end either way.

apotheon
apotheon

I owe you an apology. I mixed up your responses with someone else's, and didn't double-check to make sure I was responding to the correct person. I'm sorry about that. You're right: you did not imply anything of the sort. Some other jackass did that. re: the password manager solution itself . . . It's the best option we have for the necessity of using passwords. That's basically all there is to it, right now. We live in the real world, where we have to judge our solutions relative to the other options available to us; password managers are better than the alternatives.

Spitfire_Sysop
Spitfire_Sysop

I imply nothing of the sort. I certainly wouldn't say it's "less secure than using weak passwords". I was questioning the password manager as a solution by itself. Can it stand alone without being compared to incompetence? Let's roll back to the first sentence of my first post. "I agree with most of your points here but..." This directly implies that I agree with your opinion about passwords. You are still attacking me instead of directly addressing my concern about the password safe itself. If you aren???t going to speak to this point in this thread then just drop it. Notice I have attempted to steer this thread back to my point in every post.

apotheon
apotheon

You asked a question that very directly implied a password manager is less secure than using weak passwords.

santeewelding
santeewelding

...some years hence, when fire in his belly is replaced by ice water in his veins, completely. He's getting there. Give him time.

Spitfire_Sysop
Spitfire_Sysop

"I'd appreciate it if you'd stop trying to convince people to follow your misguided example. " Maybe I am being defensive but this looks like a personal attack to me. Who am I trying to convince of anything? What example am I leading? I have no interest in suggesting a better alternative and I never offered one. I questioned the security of using a password manager in hopes that you would have some scientific reason why it is harder to crack than the website you are logging in to. I suggested that it introduces a new attack vector. I never told anyone to use a simple password and I wouldn't. You maintain your negativity towards a concept I don't support instead of speaking about the security of the password safe itself, which is the topic of my thread. That is your problem.

apotheon
apotheon

> If the password manager is interacting with a web browser or e-mail client to enter passwords I see the potential for IE, for example, to allow access to your file system or memory. How is this even as bad as the situation where you're actually typing in the password? How is it as bad as the situation where you use the same password everywhere? How is it as bad as the situation where you use passwords so simple they can be cracked in under a minute through a simple brute force attack? > "The only problem is if you are so careless as to let it leave your possession." This is the same for paper in your pocket. You could even encrypt the writing on the paper but lets not go there. Are you serious? > Do they all exist in the same database? Not necessarily. That's up to you. > This is the very same argument that you shot down in your article so I will use your words against you: "Maybe, instead of forever, it can be cracked in an afternoon when someone invents a new approach to password cracking six months from now. Worse yet, the rate of technological advancement is accelerating exponentially." Of course. That applies to everything. The point is that using an actually strong password with a password manager allows orders of magnitude more complex passwords, which means that if "this is fun" can be cracked in an afternoon about six months from now, the password manager approach is probably not going to be that easy to crack for about sixty months. If you can crack that in an afternoon about six months from now, we're all screwed anyway, so it doesn't matter -- because it's going to take more than six months for us to change the world so passwords are not necessary without reducing security overall. > I was hoping for a discussion about the security of pwsafe and not a rant bashing my concern. You could have had it, but you decided to misinterpret points of argumentation as a personal attack. That's your problem -- not mine. Tell ya what: tell me what's a better option than a password manager. Yes, it's possible (highly unlikely, but possible) that a password manager properly handled and used will prove insufficient to protect your security. All the other even vaguely realistic options are much, much worse. If you know some super-secret technique that's better, please clue us in. Otherwise, you're welcome to avoid password managers in favor of less-security options if you want to, but I'd appreciate it if you'd stop trying to convince people to follow your misguided example.