The first password manager I ever used was a simple text file encrypted with GnuPG. When I needed a password I would decrypt the file, read it in Vim, and copy the required entry to the system clipboard. This system didn’t last. At the time I wasn’t using GnuPG for much else, and this was in the very beginning of my Vim days, when the program seemed cumbersome and daunting. I shortly moved to other, purpose-built password managers.

After some experimentation I landed on KeePassX, which I used for a number of years. Some time ago I decided that I wanted to move to a command-line solution. KeePassX and a web browser were the only graphical applications that I was using with any regularity. I could see no need for a password manager to have a graphical interface, and the GUI’s dependency on a mouse decreased my productivity. After a cursory look at the available choices I landed right back where I started all those years ago: Vim and GnuPG.

These days Vim is my most used program outside of a web browser and I use GnuPG daily for handling the majority of my encryption needs. My greater familiarity with both of these tools is one of the reasons I’ve been successful with the system this time around. I believe the other reason is my more systematic approach.

Structure

The power of this system comes from its simplicity: passwords are stored in plain text files that have been encrypted with GnuPG. Every platform out there has some implementation of the PGP protocol, so the files can easily be decrypted anywhere. After they’ve been decrypted, there’s no fancy file formats to deal with. It’s all just text, which can be manipulated with a plethora of powerful tools. I favor reading the text in Vim, but any text editor will do the job.

All passwords are stored within a directory called ~/pw. Within this directory are multiple files. Each of these files can be thought of as a separate password database. I store bank information in financial.gpg. Login information for various shopping websites are in ecommerce.gpg. My email credentials are in email.gpg. All of these entries could very well be stored in a single file, but breaking it out into multiple files allows me some measure of access control.

Access

I regularly use two computers: my laptop at home and a desktop machine at work. I trust my laptop. It has my GnuPG key on it and it should have access to all password database files. I do not place complete trust in my machine at work. I don’t trust it enough to give it access to my GnuPG key, and as such I have a different GnuPG key on that machine that I use for encryption at work.

Having passwords segregated into multiple database files allows me to encrypt the different files to different keys. Every file is encrypted to my primary GnuPG key, but only some are encrypted with my work key. Login credentials needed for work are encrypted to the work key. I have no need to login to my bank accounts at work, and it wouldn’t be prudent to do so on a machine that I do not fully trust, so the financial.gpg file is not encrypted to my work key. If someone compromises my work computer, they still will be no closer to accessing my banking credentials.

Git

The ~/pw directory is a git repository. This gives me version control on all of my passwords. If I accidentally delete an entry I can always get it back. It also provides syncing and redundant storage without depending on a third-party like Dropbox.

Keys

An advantage of using a directory full of encrypted files as my password manager is that I’m not limited to only storing usernames and passwords. Any file can be added to the repository. I keep keys for backups, SSH keys, and SSL keys (all of which have been encrypted with my GnuPG key) in the directory. This gives me one location for all of my authentication credentials, which simplifies the locating and backing up of these important files.

Markup

Each file is structured with Vim folds and indentation. There are various ways for Vim to fold text. I use markers, sticking with the default {{{/}}} characters. A typical password entry will look like this:

1
2
3
4
5

Amazon{{{
    user:   foo@bar.com
    pass:   supers3cr3t
    url:    https://amazon.com
}}}

Each file is full of entries like this. Certain entries are grouped together within other folds for organization. Certain entries may have comments so that I have a record of the false personally identifiable information the service requested when I registered.

1
2
3
4
5
6
7
8

Super Ecommerce{{{
    user:   foobar
    pass:   g0d
    Comments{{{
        birthday:   1/1/1911
        first car:  delorean
    }}}
}}}

Following a consistent structure like this makes the file easier to navigate and allows for the possibility of the file being parsed by a script. The fold markers come into play with my Vim configuration.

Vim

I use Vim with the vim-gnupg plugin. This makes editing of encrypted files seamless. When opening existing files, the contents are decrypted. When opening new files, the plugin asks which recipients the file should be encrypted to. When a file is open, leaking the clear text is avoided by disabling viminfo, swapfile, and undofile. I run gpg-agent so that my passphrase is remembered for a short period of time after I use it. This makes it easy and secure to work with (and create) the encrypted files with Vim. I define a few extra options in my vimrc to facilitate working with passwords.

 1
 2
 3
 4
 5
 6
 7
 8
 9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27

""""""""""""""""""""
" GnuPG Extensions "
""""""""""""""""""""

" Tell the GnuPG plugin to armor new files.
let g:GPGPreferArmor=1

" Tell the GnuPG plugin to sign new files.
let g:GPGPreferSign=1

augroup GnuPGExtra
" Set extra file options.
    autocmd BufReadCmd,FileReadCmd *.\(gpg\|asc\|pgp\) call SetGPGOptions()
" Automatically close unmodified files after inactivity.
    autocmd CursorHold *.\(gpg\|asc\|pgp\) quit
augroup END

function SetGPGOptions()
" Set updatetime to 1 minute.
    set updatetime=60000
" Fold at markers.
    set foldmethod=marker
" Automatically close all folds.
    set foldclose=all
" Only open folds with insert commands.
    set foldopen=insert
endfunction

The first two options simply tell vim-gnupg to always ASCII-armor and sign new files. These have nothing particular to do with password management, but are good practices for all encrypted files.

The first autocmd calls a function which holds the options that I wanted applied to my password files. I have these options apply to all encrypted files, although they’re intended primarily for use when Vim is acting as my password manager.

Folding

The primary shortcoming with using an encrypted text file as a password database is the lack of protection against shoulder-surfing. After the file has been decrypted and opened, anyone standing behind you can look over your shoulder and view all the entries. This is solved with folds and is what most of these extra options address.

I set foldmethod to marker so that Vim knows to look for all the {{{/}}} characters and use them to build the folds. Then I set foldclose to all. This closes all folds unless the cursor is in them. This way only one fold can be open at a time – or, to put it another way, only one password entry is ever visible at once.

The final fold option instructs Vim when it is allowed to open folds. Folds can always be opened manually, but by default Vim will also open them for many other cases: if you navigate to a fold, jump to a mark within a fold or search for a pattern within a fold, they will open. By setting foldopen to insert I instruct Vim that the only time it should automatically open a fold is if my cursor is in a fold and I change to insert mode. The effect of this is that when I open a file, all folds are closed by default. I can navigate through the file, search and jump through matches, all without opening any of the folds and inadvertently exposing the passwords on my screen. The fold will open if I change to insert mode within it, but it is difficult to do that by mistake.

I have my spacebar setup to toggle folds within Vim. After I have navigated to the desired entry, I can simply whack the spacebar to open it and copy the credential that I need to the system clipboard. At that point I can whack the spacebar again to close the fold, or I can quit Vim. Or I can simply wait.

Locking

The other special option I set is updatetime. Vim uses this option to determine when it should write swap files for crash recovery. Since vim-gnupg disables swap files for decrypted files, this has no effect. I use it for something else.

In the second autocmd I tell Vim to close itself on CursorHold. CursorHold is triggered whenever no key has been pressed for the time specified by updatetime. So the effect of this is that my password files are automatically closed after 1 minute of inactivity. This is similar to KeePassX’s behaviour of “locking the workspace” after a set period of inactivity.

Clipboard

To easily copy a credential to the system clipboard from Vim I have two shortcuts mapped.

1
2
3
4
5

" Yank WORD to system clipboard in normal mode
nmap <leader>y "+yE

" Yank selection to system clipboard in visual mode
vmap <leader>y "+y

Vim can access the system clipboard using both the * and + registers. I opt to use + because X treats it as a selection rather than a cut-buffer. As the Vim documentation explains:

Selections are “owned” by an application, and disappear when that application (e.g., Vim) exits, thus losing the data, whereas cut-buffers, are stored within the X-server itself and remain until written over or the X-server exits (e.g., upon logging out).

The result is that I can copy a username or password by placing the cursor on its first character and hitting <leader>y. I can paste the credential wherever it is needed. After I close Vim, or after Vim closes itself after 1 minute of inactivity, the credential is removed from the clipboard. This replicates KeePassX’s behaviour of clearing the clipboard so many seconds after a username or password has been copied.

Generation

Passwords should be long and unique. To satisfy this any password manager needs some sort of password generator. Vim provides this with its ability to call and read external commands I can tell Vim to call the standard-issue pwgen program to generate a secure 24-character password utilizing special characters and insert the output at the cursor, like this:

1

:r!pwgen -sy 24 1

Backups

The ~/pw directory is backed up in the same way as most other things on my hard drive: to Tarsnap via Tarsnapper, to an external drive via rsnapshot and cryptshot, rsync to a mirror drive. The issue with these standard backups is that they’re all encrypted and the keys to decrypt them are stored in the password manager. If I loose ~/pw I’ll have plenty of backups around, but none that I can actually access. I address this problem with regular backups to optical media.

At the beginning of every month I burn the password directory to two CDs. One copy is stored at home and the other at an off-site location. I began these optical media backups in December, so I currently have two sets consisting of five discs each. Any one of these discs will provide me with the keys I need to access a backup made with one of the more frequent methods.

Of course, all the files being burned to these discs are still encrypted with my GnuPG key. If I loose that key or passphrase I will have no way to decrypt any of these files. Protecting one’s GnuPG key is another problem entirely. I’ve taken steps that make me feel confident in my ability to always be able to recover a copy of my key, but none that I’m comfortable discussing publicly.

Shell

I’ve defined a shell function, pw(), that operates exactly like the function I use for notes on Unix.

 1
 2
 3
 4
 5
 6
 7
 8
 9
10
11

# Set the password database directory.
PASSDIR=~/pw

# Create or edit password databases.
pw() {
    cd "$PASSDIR"
    if [ ! -z "$1" ]; then
        $EDITOR $(buildfile "$1")
        cd "$OLDPWD"
    fi
}

This allows me to easily open any password file from wherever I am in the filesystem without specifying the full path. These two commands are equivalent, but the one utilizing pw() requires fewer keystrokes:

1
2

$ vim ~/pw/financial.gpg
$ pw financial

The function changes to the password directory before opening the file so that while I’m in Vim I can drop down to a shell with :sh and already be in the proper directory to manipulate the files. After I close Vim the function returns me to the previous working directory.

This still required a few more keystrokes than I like, so I configured my shell to perform autocompletion in the directory. If financial.gpg is the only file in the directory beginning with an “f”, typing pw f<tab> is all that is required to open the file.

Simplicity

This setup provides simplicity, power, and portability. It uses the same tools that I already employ in my daily life, and does not require the use of the mouse or any graphical windows. I’ve been happily utilizing it for about 6 months now.

Initially I had thought I would supplement the setup with a script that would search the databases for a desired entry, using some combination of grep, awk and cut, and then copy it to my clipboard via xsel. As it turns out, I haven’t felt the desire to do this. Simply opening the file in Vim, searching for the desired entry, opening the fold and copying the credential to the system clipboard is quick enough. The whole process, absent of typing in my passphrase, takes me only a couple of seconds.

Resources

I’m certainly not the first to come up with the idea of managing password with Vim. These resources were particularly useful to me when I was researching the possibilities:

• File encryption and password management by Conner McDaniel
• Keep passwords in encrypted file on the Vim Wiki
• Password Safe with Vim and OpenSSL by Noah

If you’re interesting in other ideas for password management, password-store and KeePassC are both neat projects that I follow.

Earlier this year I switched from Duplicity to rsnapshot for my local backups. Duplicity uses a full + incremental backup schema: the first time a backup is executed, all files are copied to the backup medium. Successive backups copy only the deltas of changed objects. Over time this results in a chain of deltas that need to be replayed when restoring from a backup. If a single delta is somehow corrupted, the whole chain is broke. To minimize the chances of this happening, the common practice is to complete a new full backup every so often – I usually do a full backup every 3 or 4 weeks. Completing a full backup takes time when you’re backing up hundreds of gigabytes, even over USB 3.0. It also takes up disk space. I keep around two full backups when using Duplicity, which means I’m using a little over twice as much space on the backup medium as what I’m backing up.

The backup schema that rsnapshot uses is different. The first time it runs, it completes a full backup. Each time after that, it completes what could be considered a “full” backup, but unchanged files are not copied over. Instead, rsnapshot simply hard links to the previously copied file. If you modify very large files regularly, this model may be inefficient, but for me – and I think for most users – it’s great. Backups are speedy, disk space usage on the backup medium isn’t too much more than the data being backed up, and I have multiple full backups that I can restore from.

The great strength of Duplicity – and the great weakness of rsnapshot – is encryption. Duplicity uses GnuPG to encrypt backups, which makes it one of the few solutions appropriate for remote backups. In contrast, rsnapshot does no encryption. That makes it completely inappropriate for remote backups, but the shortcoming can be worked around when backing up locally.

My local backups are done to an external, USB hard drive. Encrypting the drive is simple with LUKS and dm-crypt. For example, to encrypt /dev/sdb:

$ cryptsetup --cipher aes-xts-plain --key-size 512 --verify-passphrase luksFormat /dev/sdb

The device can then be opened, formatted, and mounted.

$ cryptsetup luksOpen /dev/sdb backup_drive
$ mkfs.ext4 -L backup /dev/mapper/backup_drive
$ mount /dev/mapper/backup_drive /mnt/backup/

At this point, the drive will be encrypted with a passphrase. To make it easier to mount programatically, I also add a key file full of some random data generated from /dev/urandom.

$ dd if=/dev/urandom of=/root/supersecretkey bs=1024 count=8
$ chmod 0400 /root/supersecretkey
$ cryptsetup luksAddKey /dev/sdb /root/supersecretkey

There are still a few considerations to address before backups to this encrypted drive can be completed automatically with no user interaction. Since the target is a USB drive and the source is a laptop, there’s a good chance that the drive won’t be plugged in when the scheduler kicks in the backup program. If it is plugged in, the drive needs to be decrypted before calling rsnapshot to do its thing. I wrote a wrapper script called cryptshot to address these issues.

Cryptshot is configured with the UUID of the target drive and the key file used to decrypt the drive. When it is executed, the first thing it does is look to see if the UUID exists. If it does, that means the drive is plugged in and accessible. The script then decrypts the drive with the specified key file and mounts it. Finally, rsnapshot is called to execute the backup as usual. Any argument passed to cryptshot is passed along to rsnapshot. What that means is that cryptshot becomes a drop-in replacement for encrypted, rsnapshot backups. Where I previously called rsnapshot daily, I now call cryptshot daily. Everything after that point just works, with no interaction needed from me.

If you’re interested in cryptshot, you can download it directly from GitHub. The script could easily be modified to execute a backup program other than rsnapshot. You can clone my entire backups repository if you’re also interested in the other scripts I’ve written to manage different aspects of backing up data.