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Trolling the Web of Trust

This repository is the home of scripts related to my OHM2013 talk.

To get started, clone the repo and submodules:

git clone
cd trollwot
git submodule init
git submodule update

Install some dependencides. On a Debian-based distro you do this:

sudo apt-get install python-psutil monkeysphere

Install the gnupg build dependencies. On a Debian-based distro you do this:

sudo apt-get build-dep gnupg

Build the modified gnupg.

cd lib/gnupg

ASCII sign a PGP key

ascii_sign is a script that takes a filename and a target key id as input. It downloads the target key, then generates a new PGP for each line in the file and signs the target key with the new keys. Essentially, it lets you sign any key with ASCII art.

For example, check out my key:

ASCII sign a key like this:


If you're ASCII signing a key with multiple user IDs, you'll have to press "y" to verify you want to sign all user IDs for each line.

Add fake sigs to a PGP key is a script that takes a name, email address, and target key id as input. It creates a new key with that name and email, and uses it to sign the target key. Usage:

./fake_sign [NAME] [EMAIL] [KEYID]

Brute force PGP key ID is a modified version of the keytrans script, that comes with monkeysphere that adds new functionality to do the brute forcing. Since:

fingerprint = hash(public_key)
public_key = timestamp + public_key_data


fingerprint = hash(timestamp + public_key_data)

So the script works like this:

  • It generates a 4096 bit RSA key
  • It sets the creation timestamp to now
  • It goes in a loop calculating the fingerprint and looking for collisions, decrementing the timestamp until the timestamp is from 3 years ago
  • If it didn't find it, it starts over by generating a new 4096 bit RSA key

On my laptop it compares about 12,000 fingerprints per second. Here's how to use it:

./bruteforce_keyid [USERID] [KEYID]

Note: The keys generated by this script are likely cryptographically secure, but sadly they don't seem to actually work to do crypto operations. For example:

[user@gpgvm ~]$ gpg --homedir vanity_homedir/ --list-secret-keys 
sec   4096R/22222222 2014-03-10
uid                  Micah Lee <>

sec   4096R/CCCCCCCC 2014-01-12
uid                  Micah Lee <>

sec   4096R/D15C0FAD 2014-01-26
uid                  Micah Lee <>

sec   4096R/D15EA5ED 2014-02-07
uid                  Micah Lee <>

sec   4096R/FAC701D5 2014-05-01
uid                  Micah Lee <>

sec   4096R/FEE1DEAD 2014-02-08
uid                  Micah Lee <>

sec   4096R/00000001 2013-12-05
uid                  Micah Lee <>

[user@gpgvm ~]$ gpg --homedir vanity_homedir/ --default-key D15EA5ED --detach-sign test 
gpg: no default secret key: unusable secret key
gpg: signing failed: unusable secret key

If anyone wants to fix this problem, pull requests are welcome.


Trolling the Web of Trust







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