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PIUS: The PGP Individual UID Signer

CircleCI

Introduction

Signing keys after a PGP Keysigning party can take a lot of time. Further, it's very difficult to do right: signing each UID separately and emailing it off is not something tools make easy. I wanted to solve both of those problems and make signing keys the right and most secure way easier and faster. PIUS and its related tools make this process simple, faster, and easier to get right.

Usage

The most common way to use PIUS is with a keyring from a keysigning party, like this:

$ pius -A -s <your_keyid> -r <path_to_keyring> -m <your_email>

For every key (-A) on the keyring (-r) this will prompt you to verify the fingerprint and choose a signing level. Then, if you tell it to, it will sign all UIDs on <keyid>, and export one copy of the key for each UID with only that UID signed. Each one will then be encrypt-emailed off to the email address in the UID (-m). Finally, -s tells it which key to sign with.

There are a variety of other options that you may want:

  • customize the tmpdir and outdir directories (-t and -o respectively)
  • encrypt the outfiles to <filename>_ENCRYPTED.asc (-e)
  • import the unsigned keys to the default keyring (-I)
  • verbose mode (-v)
  • customize mail hostname and port (-H and -P respectively)
  • customize the email message (-M)
  • don't use PGP/Mime in the email (-O, implies -e)
  • specify a SMTPAUTH or STARTTLS for SMTP (-u and -S)

And more! See the '-h' option for more.

Security Implications

The default mode for PIUS, starting in 2.2.0 is agent mode. If you are using gpg2 this is the only valid mode.

If you aren't using gpg2, there are some other options. If you use cache_passphrase mode. This means that PIUS will ask you for your passphrase at startup, verify this passphrase is correct, and then feed it GnuPG everytime it needs it. The passphrase is stored in memory and only for the life of the execution of PIUS. For most users this should be relatively safe. However, it is worth noting that if you are on a machine whose system administrators you don't trust, there is a small danger of them reading this memory while PIUS is running.

Finally we have interactive mode which can be entered using -i. This will use pexpect to handle most of the signing interactions and then drop you into the 'gpg --edit-key' shell whenever gpg needs a passphrase. Using this you can enter your passphrase directly into gpg. This mode has two main disadvantages. The first is that the pexpect code is quite fragile, and the second is that you'll have to type your passphrase for every key-UID combination.

Both interactive and cache_passphrase mode will be removed in the next version when gpg1 support is dropped.

Sending Emails

When PIUS emails out keys it BCC's you, so you will get a copy of every email sent out. If you would like to see what is going to be sent and not have it sent, you can either do:

$ pius -T

To have PIUS dump the text of the default email body, or you can use the -n option to forcefully override the TO in the envelope of the email. When doing this only the address specified as an argument to -n will get the email.

If you want to see the email sent when not using PGP/Mime then try:

$ pius -T -O

If you want to customize this message you can do so with the -M option. Note that you may use python's named variable interpolation syntax here to have PIUS fill in email (the email in the UID, i.e. the recipient), keyid (of the key that was signed), and signer (the keyid used to sign, i.e. your keyid). For example, you can simply include "%(keyid)s" (without the quotes) to get the keyid.

PIUS's default config assumes there is a local mail delivery agent (MDA) available on port 587. If this is not the case for you, you'll want to specify your mail server's information using -H for smtp host, -p for port, and -u for username. For example, for GMail you might use:

-H smtp.gmail.com -p 587 -u <your_email@gmail.com>

I recommend you add these settings to your config file so you don't have to type them every time. See the Config File section below.

Note that if you've setup 2-factor authentication with your mail provider, you will need an app-password for this to work. For GMail, see their docs.

Other Platforms

On non-UNIX platforms such as MacOS and Windows, the default gpg path will likley be incorrect, so you'll want to use -b to specify the path.

Config File

You can specify options you'd like to always use in a ~/.pius/piusrc file. The format of this file is option=value. The "=value" part is obviously not required for options that don't have a value. An example might be:

mail=you@sample.com
tmp-dir=/home/you/pius/tmp
use-agent

PIUS will accept =, : or whitespace as a separator, and will handle extra whitespace around any separator.

History

PIUS started life as a group of bad shell scripts I had thrown together through the years after going to various PGP keysigning parties. These scripts automated various bits and pieces of signing various keys and UIDs, but fell short of actually making it a mostly painless process.

Finally I decided to sit down and combine all these shell scripts into a single unified utility to make signing individual UIDs on a multitude of keys as painless as possible. Since this was going to be mostly forking off gpg instances, it seemed like shell was the way to go. However, after dealing with gpg and its "API" for a while, I quickly realized that was not going to be the best course of action. Since I wanted an excuse to write more python, instead of my usual perl, I decided to write this in python.

The original version heavily used the pexpect module for various reasons: (1) I wanted to be able to let the user enter the passphrase directly into gpg for security reasons, (2) Using the --{command,passphrase,status}-fd options turned not to be not that well documented and not work the way the documentation suggested.

This method quickly showed itself to be very fragile. So, I managed to bend gpg to my will without using pexpect, and the only thing left that uses pexpect is the 'interactive' mode, which will probably one day go away if gpg-agent becomes reliable enough.

License

PIUS is released under the GNU Public License v2 and is Copyright Phil Dibowitz <phil@ipom.com>.

Phil Dibowitz

phil@ipom.com

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