A look at password managers

As we noted in an earlier article, passwords are a liability and we'd prefer to get rid of them, but the current reality is that we do use a plethora of passwords in our daily lives. This problem is especially acute for technology professionals, particularly system administrators, who have to manage a lot of different machines. But it also affects regular users who still use a large number of passwords, from their online bank to their favorite social-networking site. Despite the remarkable memory capacity of the human brain, humans are actually terrible at recalling even short sets of arbitrary characters with the precision needed for passwords.

Therefore humans reuse passwords, make them trivial or guessable, write them down on little paper notes and stick them on their screens, or just reset them by email every time. Our memory is undeniably failing us and we need help, which is where password managers come in. Password managers allow users to store an arbitrary number of passwords and just remember a single password to unlock them all.

But there is a large variety of password managers out there, so which one should we be using? At my previous job, an inventory was done of about 40 different free-software password managers in different stages of development and of varying quality. So, obviously, this article will not be exhaustive, but instead focus on a smaller set of some well-known options that may be interesting to readers.

KeePass: the popular alternative

The most commonly used password-manager design pattern is to store passwords in a file that is encrypted and password-protected. The most popular free-software password manager of this kind is probably KeePass.

An important feature of KeePass is the ability to auto-type passwords in forms, most notably in web browsers. This feature makes KeePass really easy to use, especially considering it also supports global key bindings to access passwords. KeePass databases are designed for simultaneous access by multiple users, for example, using a shared network drive.

KeePass has a graphical interface written in C#, so it uses the Mono framework on Linux. A separate project, called KeePassX is a clean-room implementation written in C++ using the Qt framework. Both support the AES and Twofish encryption algorithms, although KeePass recently added support for the ChaCha20 cipher. AES key derivation is used to generate the actual encryption key for the database, but the latest release of KeePass also added using Argon2, which was the winner of the July 2015 password-hashing competition. Both programs are more or less equivalent, although the original KeePass seem to have more features in general.

The KeePassX project has recently been forked into another project now called KeePassXC that implements a set of new features that are present in KeePass but missing from KeePassX like:

• auto-type on Linux, Mac OS, and Windows
• database merging — which allows multi-user support
• using the web site's favicon in the interface

So far, the maintainers of KeePassXC seem to be open to re-merging the project "if the original maintainer of KeePassX in the future will be more active and will accept our merge and changes". I can confirm that, at the time of writing, the original KeePassX project now has 79 pending pull requests and only one pull request was merged since the last release, which was 2.0.3 in September 2016.

While KeePass and derivatives allow multiple users to access the same database through the merging process, they do not support multi-party access to a single database. This may be a limiting factor for larger organizations, where you may need, for example, a different password set for different technical support team levels. The solution in this case is to use separate databases for each team, with each team using a different shared secret.

Pass: the standard password manager?

I am currently using password-store, or pass, as a password manager. It aims to be "the standard Unix password manager". Pass is a GnuPG-based password manager that features a surprising number of features given its small size:

• copy-paste support
• Git integration
• multi-user/group support
• pluggable extensions (in the upcoming 1.7 release)

The command-line interface is simple to use and intuitive. The following, will, for example, create a pass repository, a 20 character password for your LWN account and copy it to the clipboard:

    $ pass init
    $ pass generate -c lwn 20

The main issue with pass is that it doesn't encrypt the name of those entries: if someone were to compromise my machine, they could easily see which sites I have access to simply by listing the passwords stored in ~/.password-store. This is a deliberate design decision by the upstream project, as stated by a mailing list participant, Allan Odgaard:

Odgaard goes on to point out that there are alternatives that do encrypt the entire database (including the site names) if users really need that feature.

Furthermore, there is a tomb plugin for pass that encrypts the password store in a LUKS container (called a "tomb"), although it requires explicitly opening and closing the container, which makes it only marginally better than using full disk encryption system-wide. One could also argue that password file names do not hold secret information, only the site name and username, perhaps, and that doesn't require secrecy. I do believe those should be kept secret, however, as they could be used to discover (or prove) which sites you have access to and then used to perform other attacks. One could draw a parallel with the SSH known_hosts file, which used to be plain text but is now hashed so that hosts are more difficult to discover.

Also, sharing a database for multi-user support will require some sort of file-sharing mechanism. Given the integrated Git support, this will likely involve setting up a private Git repository for your team, something which may not be accessible to the average Linux user. Nothing keeps you, however, from sharing the ~/.password-store directory through another file sharing mechanism like (say) Syncthing or Dropbox.

You can use multiple distinct databases easily using the PASSWORD_STORE_DIR environment variable. For example, you could have a shell alias to use a different repository for your work passwords with:

    alias work-pass="PASSWORD_STORE_DIR=~/work-passwords pass"

Group support comes from a clever use of the GnuPG multiple-recipient encryption support. You simply have to specify multiple OpenPGP identities when initializing the repository, which also works in subdirectories:

    $ pass init -p Ateam me@example.com joelle@example.com
    mkdir: created directory '/home/me/.password-store/Ateam'
    Password store initialized for me@example.com, joelle@example.com
    [master 0e3dbe7] Set GPG id to me@example.com, joelle@example.com.
     1 file changed, 2 insertions(+)
     create mode 100644 Ateam/.gpg-id

The above will configure pass to encrypt the passwords in the Ateam directory for me@example.com and joelle@example.com. Pass depends on GnuPG to do the right thing when encrypting files and how those identities are treated is entirely delegated to GnuPG's default configuration. This could lead to problems if arbitrary keys can be injected into your key ring, which could confuse GnuPG. I would therefore recommend using full key fingerprints instead of user identifiers.

Regarding the actual encryption algorithms used, in my tests, GnuPG 1.4.18 and 2.1.18 seemed to default to 256-bit AES for encryption, but that has not always been the case. The chosen encryption algorithm actually depends on the recipient's key preferences, which may vary wildly: older keys and versions may use anything from 128-bit AES to CAST5 or Triple DES. To figure out which algorithm GnuPG chose, you may want to try this pipeline:

    $ echo test | gpg -e -r you@example.com | gpg -d -v
    [...]
    gpg: encrypted with 2048-bit RSA key, ID XXXXXXX, created XXXXX
	  "You Person You <you@example.com>"
    gpg: AES256 encrypted data
    gpg: original file name=''
    test

As you can see, pass is primarily a command-line application, which may make it less accessible to regular users. The community has produced different graphical interfaces that are either using pass directly or operate on the storage with their own GnuPG integration. I personally use pass in combination with Rofi to get quick access to my passwords, but less savvy users may want to try the QtPass interface, which should be more user-friendly. QtPass doesn't actually depend on pass and can use GnuPG directly to interact with the pass database; it is available for Linux, BSD, OS X, and Windows.

Browser password managers

Most users are probably already using a password manager through their web browser's "remember password" functionality. For example, Chromium will ask if you want it to remember passwords and encrypt them with your operating system's facilities. For Windows, this encrypts the passwords with your login password and, for GNOME, it will store the passwords in the gnome-keyring storage. If you synchronize your Chromium settings with your Google account, Chromium will store those passwords on Google's servers, encrypted with a key that is stored in the Google Account itself. So your passwords are then only as safe as your Google account. Note that this was covered here in 2010, although back then Chromium didn't synchronize with the Google cloud or encrypt with the system-level key rings. That facility was only added in 2013.

In Firefox, there's an optional, profile-specific master password that unlocks all passwords. In this case, the issue is that browsers are generally always open, so the vault is always unlocked. And this is for users that actually do pick a master password; users are often completely unaware that they should set one.

The unlocking mechanism is a typical convenience-security trade-off: either users need to constantly input their master passwords to login or they don't, and the passwords are available in the clear. In this case, Chromium's approach of actually asking users to unlock their vault seems preferable, even though the developers actually refused to implement the feature for years.

Overall, I would recommend against using a browser-based password manager. Even if it is not used for critical sites, you will end up with hundreds of such passwords that are vulnerable while the browser is running (in the case of Firefox) or at the whim of Google (in the case of Chromium). Furthermore, the "auto-fill" feature that is often coupled with browser-based password managers is often vulnerable to serious attacks, which is mentioned below.

Finally, because browser-based managers generally lack a proper password generator, users may fail to use properly generated passwords, so they can then be easily broken. A password generator has been requested for Firefox, according to this feature request opened in 2007, and there is a password generator in Chrome, but it is disabled by default and hidden in the mysterious chrome://flags URL.

Other notable password managers

Another alternative password manager, briefly mentioned in the previous article, is the minimalistic Assword password manager that, despite its questionable name, is also interesting. Its main advantage over pass is that it uses a single encrypted JSON file for storage, and therefore doesn't leak the name of the entries by default. In addition to copy/paste, Assword also supports automatically entering passphrases in fields using the xdo library. Like pass, it uses GnuPG to encrypt passphrases. According to Assword maintainer Daniel Kahn Gillmor in email, the main issue with Assword is "interaction between generated passwords and insane password policies". He gave the example of the Time-Warner Cable registration form that requires, among other things, "letters and numbers, between 8 and 16 characters and not repeat the same characters 3 times in a row".

Another well-known password manager is the commercial LastPass service which released a free-software command-line client called lastpass-cli about three years ago. Unfortunately, the server software of the lastpass.com service is still proprietary. And given that LastPass has had at least two serious security breaches since that release, one could legitimately question whether this is a viable solution for storing important secrets.

In general, web-based password managers expose a whole new attack surface that is not present in regular password managers. A 2014 study by University of California researchers showed that, out of five password managers studied, every one of them was vulnerable to at least one of the vulnerabilities studied. LastPass was, in particular, vulnerable to a cross-site request forgery (CSRF) attack that allowed an attacker to bypass account authentication and access the encrypted database.

Problems with password managers

When you share a password database within a team, how do you remove access to a member of the team? While you can, for example, re-encrypt a pass database with new keys (thereby removing or adding certain accesses) or change the password on a KeePass database, a hostile party could have made a backup of the database before the revocation. Indeed, in the case of pass, older entries are still in the Git history. So access revocation is a problematic issue found with all shared password managers, as it may actually mean going through every password and changing them online.

This fundamental problem with shared secrets can be better addressed with a tool like Vault or SFLvault. Those tools aim to provide teams with easy ways to store dynamic tokens like API keys or service passwords and share them not only with other humans, but also make them accessible to machines. The general idea of those projects is to store secrets in a central server and send them directly to relevant services without human intervention. This way, passwords are not actually shared anymore, which is similar in spirit to the approach taken by centralized authentication systems like Kerberos. If you are looking at password management for teams, those projects may be worth a look.

Furthermore, some password managers that support auto-typing were found to be vulnerable to HTML injection attacks: if some third-party ad or content is able to successfully hijack the parent DOM content, it masquerades as a form that could fool auto-typing software as demonstrated by this paper that was submitted at USENIX 2014. Fortunately, KeePass was not vulnerable according to the security researchers, but LastPass was, again, vulnerable.

Future of password managers?

All of the solutions discussed here assume you have a trusted computer you regularly have access to, which is a usage pattern that seems to be disappearing with a majority of the population. You could consider your phone to be that trusted device, yet a phone can be lost or stolen more easily than a traditional workstation or even a laptop. And while KeePass has Android and iOS ports, those do not resolve the question of how to share the password storage among those devices or how to back them up.

Password managers are fundamentally file-based, and the "file" concept seems to be quickly disappearing, faster than we technologists sometimes like to admit. Looking at some relatives' use of computers, I notice it is less about "files" than images, videos, recipes, and various abstract objects that are stored in the "cloud". They do not use local storage so much anymore. In that environment, password managers lose their primary advantage, which is a local, somewhat offline file storage that is not directly accessible to attackers. Therefore certain password managers are specifically designed for the cloud, like LastPass or web browser profile synchronization features, without necessarily addressing the inherent issues with cloud storage and opening up huge privacy and security issues that we absolutely need to address.

This is where the "password hasher" design comes in. Also known as "stateless" or "deterministic" password managers, password hashers are emerging as a convenient solution that could possibly replace traditional password managers as users switch from generic computing platforms to cloud-based infrastructure. We will cover password hashers and the major security challenges they pose in a future article.