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New Year, New Password Manager, Part Deux

Back during the Before Times™, I set out on a quest to free my passwords and various other credentials from the walled garden of the Apple ecosystem, and was fairly satisfied with my first attempt at a solution. Six months later, and, well, you can probably guess by the fact that you’re reading this that things were not so peachy, and you’d be right. So what went wrong? A few minor quibbles here and there, with one annoyance substantial enough to drive me back to the drawing board: That pandora’s box we all unwittingly unleash upon ourselves the moment we find ourselves with more than one device: synchronization.

In my first post about KeePass, I naïvely hand-waved away the problem of synchronization onto the clients, blissfully unaware of how ill-equipped many were to the task. The principle problem, I believe, lies in the fact that KeePass stores everything in a single binary file. A change to one password affects every password, from the perspective from a client. While backing up one’s database is as simple as copying a file, there was nonetheless much apprehension whenever a sync was required. So, back at the drawing board, I’ve added a requirement of easy conflict resolution. Reviewing my list of available options, I eased my requirement of widespread availability, and settled on pass, "the standard unix password manager".

pass is made with the Unix philosophy in mind; it does one thing, and it does it well, namely retrieving passwords and orchestrating other tools to save (any editor you’d like), encrypt (gpg) passwords in a versioned (git) repository. Oh, and passwords are saved as individual files, because everything is a file. With version control being handled by git, I think it’s safe to say that the “easy conflict resolution” box can be checked.

Synchronization across devices works in a similar fashion to multiple persons collaborating on a project with Git; each device holds a local copy of the password store, pushing and pulling updates to and from one another. For simplicities sake, I’ve opted to establish a central repository hosted on a private server using NGINX.

Providing Password Protection

Although our passwords are individually encrypted, it’s probably still a good idea to password-protect the repository endpoint on the server. There are a variety of ways this can be accomplished; one of the simplest being with htpasswd. Add a user like so (you may omit the -c flag if a credential file already exists):

$
htpasswd -c /etc/nginx/.htpasswd

Serving the Password Store

Serving a Git repository with NGINX is relatively straight-forward. We can simply pass any requests to git-http-backend via FastCGI. Like password protection, it’s probably a good idea to secure the endpoint with SSL as well. Thankfully, this can be achieved with virtually no effort thanks to Let’s Encrypt. I’ll leave that part of the process as an exercise for the reader.

server {
listen 443 ssl;
server_name my.domain.com;
root /var/www/pass;
ssl_certificate /etc/nginx/ssl/nginx.crt;
ssl_certificate_key /etc/nginx/ssl/nginx.key;
access_log /var/log/nginx/pass.access.log;
error_log /var/log/nginx/pass.error.log;
auth_basic "Authentication required";
auth_basic_user_file /etc/nginx/.htpasswd;
location / {
client_max_body_size 0; # git pushes can be massive, make sure nginx doesn't abruptly cut the connection
include /etc/nginx/fastcgi_params;
fastcgi_param SCRIPT_FILENAME /usr/libexec/git-core/git-http-backend;
fastcgi_param GIT_HTTP_EXPORT_ALL "";
fastcgi_param GIT_PROJECT_ROOT /var/www/pass; # directory containing repositories
fastcgi_param PATH_INFO $uri;
fastcgi_param REMOTE_USER $remote_user;
fastcgi_pass unix:/var/run/fcgiwrap.socket; # pass the request to fastcgi
}
}

Tug of War

Git relies on the concepts of “pushing” and “pulling” to update others and receive updates from others, respectively. Unfortunately, these are manual processes. We can automate pushing though, through the use of commit hooks, as pass automatically commits changes. Hooks are simply executables, such as a bash script, that are run by git at various stages of the commit process. For our purposes of automatically pushing updates, we can use a post-commit hook. To do so, add an executable file to /path/to/your/.password-store/.git/hooks/post-commit containing the following:

#!/bin/sh
git push origin master

Automating pulling updates is a little more tricky. Perhaps a hook could be written to regularly run git pull, or some solution using push notifications from the server could be architected. I’ll leave this as an exercise to the reader or my future self.

Déjà-vu All Over Again

Because I like the idea of symmetry with the first post, here’s a list of clients I’m currently using:

  • pass, obviously.

  • passff, a Firefox addon for web integration.

  • Pass, an iOS client.

Conclusion

I’m excited to be continuing taking steps towards a more private, personal infrastructure for my data. In particular, pass, with its philosophy of being a focused, composable application, represents freedom not only for my data, but for my workflow and the tools supporting it.

❋❋❋

In Praise of Tinkering

If you’re reading this, it’s a good bet that you’re a tinkerer like me. I love tweaking and tailoring just about everything I can, to the point that it’s probably confusing that I’m not a Plasma user. To which I say, I believe that form follows function, not that function negates the need for form completely (You can send your complaints to $NAME_OF_OTHER_PODCAST_HOST). Despite being a perfectly defendable position epistemically speaking, I don’t believe that everyone is a bot except me, and instead tend to believe that my fellow developers like to tinker as well, to the point that I’m always rather surprised and a little hurt when I hear others say that they’d rather stick to the beaten path; that they don’t want to customize their operating systems more than they absolutely have to. Don’t get me wrong, I’m not saying you’re a bad person if you’ve never felt the desire to make your windows wobbly (@Plasma users), I’m with you there, but I’m not going to subject myself to using bash as my default shell because I have to SSH into servers on at least a weekly basis and am worried about being slightly uncomfortable in this context. It’s a fraction of my time and I’m significantly more productive with the rest of the time using Fish. Not only that, but my comfort with Fish was what encouraged me to dive deeper into shell scripting; something I had previously tried to avoid to a fault, writing ridiculous python scripts that could have been implemented trivially with a handful of pipes in a one-liner.

This is a common manifestation of the most frequently cited reasons I see given against tinkering: the fear of losing the fruits of ones labor, be it because one has been forced into a situation of using a stock system, such as in the case of the aforementioned SSH session, or from data loss, such as after setting up a new OS. To the former I say, don’t copy-paste configs if you don’t know what they do. Any tinkering you do ought to be done reversibly, i.e. that you only do it if you at least generally understand what you’ve done and how your modified configuration differs from the original, and have some kind of version control in place (More on that below). Don’t remap “:” to “;” if you’re worried that you won’t be able to remember how to use vanilla vi.

To the people worried about losing their configurations, this is a little more understandable as it requires some actual effort to rectify, but not much. There are a myriad of solutions available for not only backing up your configurations (also known as “dotfiles” because they’re frequently stored in hidden files and directories), such as GNU Stow or (my personal favorite) Dotdrop. You can also write installation scripts for the parts that can’t be handled by symlinking dotfiles from a git repo. I have a small collection for mine, and GitHub has an entire page dedicated to the documenting some of the most masterful dotfile setups. Even if you aren’t a DevOps engineer, maintaining a git repo and drafting a few shell scripts isn’t bad practice of the kinds of hard skills that every developer needs.

Finally, I’d like to address the idea of our machines being mere tools, disposable if anything goes wrong. I completely agree with the latter half of this sentiment. I don’t know if I should be admitting this, but I tend to hose my machine at least once or twice a year. I do something so incredibly stupid that I either have to completely reinstall the OS, or worse, I’ve accidentally deleted it while trying to reformat another partition or something. It used to be a horrific event, with repercussions rippling outward days into the future as I slaved over restoring every bit back to its proper place, clicking checkboxes and re-downloading installers. Now, everything I need is backed up onto multiple media in multiple physical locations and my current configuration is a shell script away. I could throw my computer into a lake and be able to pretend like nothing ever happened within a couple of hours. My computer has been effectively disposable for the past year and a half now, and tinkering with configuration management is the reason why.

To the people who want to see their machines as mere tools, I say they already are. They always have been! They’re functionally-equivalent to a hammer in the grand scheme of things. The only difference being that instead of providing mechanical leverage, their’s is computational. As an implementation, they’re actually worse than their physical counterparts. If you’ve ever handled old tools, you’ll have noticed how they wear. Their handles erode in such a way that your hand fits them perfectly. They’ve been sculpted over years of use. Computers, namely operating systems, don’t exhibit such a property. Without the effort, their sharp edges will remain as sharp as they day they were compiled until the bit rot finally breaks them. They’re almost brittle in this regard. We can smooth those edges though, with a little effort and a bit of tinkering.

Since we’re all stuck inside for an indeterminate length of time into the future, use some of it to sand some sharp edges. Try a new shell! Make some aliases for frequently-used commands! Write a program that nags you when you inevitably don’t use them for the first few weeks! Ruminate about why you didn’t do this sooner!

But above all, stay safe. We’ll see you on the other side.

#andràtuttobene 🇮🇹

❋❋❋

New Year, New Password Manager

The walled garden of the Apple ecosystem is certainly a cozy one, but good luck if you ever want to venture out beyond into other realms, such as Linux. For some use cases, iCloud is not only perfectly fine, but even preferable. I don’t foresee myself needing access to my Shortcuts on any non-iOS devices, so I can’t say I have any real qualms about cordoning them off onto their own platform. My documents, on the other hand? That’s another story. Likewise, what about photos and, probably most importantly, passwords? To put it succinctly, I want a solution that lets me have access to only what I need on each device/OS that I use, and nothing more. 2020 has brought some new themes for me; one of which is action. I’ve decided that the first step I’m going to take towards achieving world domination my goal is tackling the most important domain: passwords.

As aforementioned, things are pretty great within the confines of the walled garden; though by no means is it a panacea. The Keychain app has some pretty gaping holes with regard to its capabilities on each of the various platforms. On macOS, it’s pretty great! There’s a good concept of the different kinds of information that can be securely stored within it: login passwords, keys, notes, etc. Sadly, this notion does not translate over to iOS, and that’s a problem. Reinstalling macOS and the encryption key of your backup is stored in a secure note? You better write that down ahead of time or have another Mac around. May the gods have pity on you if you need to access any passwords on a device that isn’t logged into your iCloud account, or *gasp* isn’t running an Apple OS.

There are myriad third-party password managers. I prefer open source solutions where possible, so I first tried Bitwarden. It’s… okay. It does tick all the big boxes that Apple’s first-party solutions do, with the added benefits of having a web app (!) and being much more cross-platform. I understand why all of the clients are Electron/React-based, but I much prefer native apps. Being open source, and seeing some existing attempts at native clients, I thought I’d try to revive one. In doing so, I see why it stagnated: there’s little to no documentation, both outside of and within the source.

Enter: KeePass

KeePass is more of a protocol than a platform, and this is how it shines! There are native clients for just about every OS (at least that I use), and syncing it is as simple as passing a single file, the database, around through whatever means you please (in my case, Nextcloud). Clients can take care of merging or reverting changes as needed.

Hello darkness Applescript, my old friend…

Migrating between proprietary applications is never without hiccups, and Apple usually does a better job than most at enabling interoperablilty *cough* Microsoft *cough*. Keychain.app though, is the absolute antithesis of this. I understand that a password manager should probably have additional safeguards in place around data export, but crippling that functionality is not a safeguard. Login passwords, such as internet passwords, cannot be exported. The category of secure items that I most likely need available to me on other platforms is the hardest thing to extract. Having almost 250 login items in Keychain, I was not about to type my password in for each. Thankfully, there’s an App[lescript] for That™. I had to modify it to work on 10.14.6+, and if you’re reading this more than six months from date of publication, I’m sorry that you’ll probably have to modify it further to work for yourself, but here, in all of its horrendous glory, is a script to copy a given number of items from Keychain.app to a csv file.

set x to 1
tell application "Keychain Access"
activate
repeat while (x ≤ NUMBER_OF_ITEMS_TO_EXPORT)
tell application "System Events"
click text field 1 of row 1 of outline 1 of scroll area 1 of splitter group 1 of window "Keychain Access" of application process "Keychain Access"
keystroke return
delay 0.2
keystroke tab
delay 0.2
keystroke tab
delay 0.2
keystroke tab
delay 0.2
keystroke "c" using command down
delay 0.2
do shell script "/usr/bin/pbpaste | xargs -I {} echo -n {}\",\" >> ~/exports.csv"
delay 0.2
keystroke tab using shift down
delay 0.2
keystroke "c" using command down
delay 0.2
do shell script "/usr/bin/pbpaste | xargs -I {} echo -n {}\",\" >> ~/exports.csv"
delay 0.2
click checkbox "Show password:" of tab group 1 of window 1 of application process "Keychain Access"
delay 0.2
keystroke KEYCHAIN_PASSWORD
delay 0.2
keystroke return
delay 0.2
keystroke tab using shift down
delay 0.2
keystroke tab using shift down
delay 0.2
keystroke tab using shift down
delay 0.2
keystroke "c" using command down
delay 0.2
do shell script "/usr/bin/pbpaste | xargs -I {} echo {}\",\" >> ~/exports.csv"
delay 0.2
click UI element 2 of window 1 of application process "Keychain Access"
delay 0.2
key code 125
delay 0.2
end tell
set x to (x + 1)
end repeat
end tell

You’ll want to substitute the number of items, as well as your password, and beware that it obviously exports them as plaintext (in plain text), so don’t save it to your Documents or Desktop folders if those are synced via iCloud. Additionally, you can sort items by “Kind” if you’re only interested in exporting certain types, such as login items. Then sit back, relax, maybe prepare a beverage, because it might take a while (About a half of an hour, in my case).

Part the Second, Converting to KeePass

KeePass has a diverse ecosystem of scripts and utilities for importing a variety of data formats through a client. For our purposes, there’s csv2keepassxml, an incredibly flexible Ruby utility that converts data from, you guessed it, csv into an importable xml file. If, unlike me, you’re a Ruby expert or don’t care about littering your system with packages you’ll install once and probably never use again, feel free to skip the next two sections.

rbenv

Because I wasn’t developing web apps in 2008, I’m not a big fan of Ruby, but I am a fan of using virtual environments, especially for languages with system installations, such as Python and, you guessed it, Ruby, on macOS (for now). If you don’t care about such things, feel free to skip this section. For everyone else, there’s rbenv. Much like its Python counterpart, pyenv, installation is simple and can be accomplished via brew.

$
brew install rbenv

Follow the instructions given by the init command to set up your shell.

$
rbenv init

Finally, source your config or restart your terminal to make the changes take effect.

Usage is equally simple. To install a far more up-to-date version of Ruby than what macOS may (or in the future may not) even have, simply use the install command.

$
rbenv install

rbenv-gemset

Virtual environments aren’t terribly useful without dependency management. For rbenv, this is where rbenv-gemset comes in. A plugin for rbenv, it allows dependencies to be managed per-project and even reside within the project directory.

Installation is as easy as rbenv, as it’s also available via brew.

$
brew install rbenv-gemset

In the root of the project, create a gemset using the current version of Ruby.

$
rbenv gemset init

You can now use gem as you would normally, with the gems being installed to a directory in the root of your project.

csv2keepassxml

If you’re joining us from the beginning of this part, welcome back! csv2keepassxml is available not via brew, so let’s clone the repository from Github.

$
git clone https://github.com/lifepillar/csv2keepassxml

Create a gemset, and install csv2keepassxml's dependencies into it.

$
gem install htmlentities

If you used the format of the aforementioned applescript, the following will create a KeePass2 database file from the exported csv file.

$
./csv2keepassxml -t 1 -U 1 -u 2 -p 3 ~/keychain-export.csv

Note: Indices are 1-based. Unfortunately.

Clients, Clients Everywhere!

There are a plethora of KeePass clients out there. Here are the ones that I use, and for the most part recommend. For an added bonus, they’re all open source!

Conclusion

This is the first step in my journey towards building a private infrastructure for my personal data. Over the upcoming months, I’ll be looking into solutions for file storage and syncing, and then eventually services such as email, contacts, and calendars.