Installation, configuration and security hardening guidance for DeadDrop
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The documentation has been merged into the main repository at freedomofpress/securedrop.

Deaddrop Environment Install Guide

Deaddrop is a tool for communicating securely with journalists. Please also view the Threat_Model.doc, diagram.jpg, and design.jpg in docs/ for more information. The environment install guide is below the license.

Copyright (C) 2011-2013 James Dolan

This program is free software: you can redistribute it and/or modify it under the terms of the GNU Affero General Public License as published by the Free Software Foundation, either version 3 of the License, or (at your option) any later version.

This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the GNU Affero General Public License for more details.

You should have received a copy of the GNU Affero General Public License along with this program. If not, see

Hardware Requirements

The following equipment will be required:
1. You will need 3 computers with the hard drives still installed
2. You will need 1 computer shell (a computer with the hard drive removed)
3. You will need 3 USB sticks with Tails the Amesic Incognito Live System installed
4. You will need 2 USB sticks for transfering files
5. You will need 1 USB stick for storing the applications gpg private key
6. A USB stick will be needed for each journalist for storing their personnel gpg private keys

Local Certificate Authority Install

The journalist's interface uses ssl certificates for transport encryption and authentication that will be generated on the Local CA USB stick.

  1. Steps to download, verify and install Tails to a usb stick can be found here
  2. Step to configure the Personal Data persistant storage feature to store the config file and root CA certs can be found here
  3. Ensure that Persistent Volume Feature 'Personal Data' is activated
  4. The Local CA never needs to be connected to a network to generate the needed certificates and revocation lists
  5. The USB stick that the Local CA is installed on should be stored securely when not in use
  6. The USB stick that the Local CA is installed on should be clearly labeled to avoid confusion with other USB sticks
  7. User certificates should only be generated for approved journalists that require access to the journalist interface
  8. Unique user certificates should be generated for each approved journalist
  9. User certificates should be securely transported to the approved journalist
  10. Server and user certificates should be set to expire to your organization's policy
  11. A User certificate should be revoked if the journalist no longer requires access

Setup openssl

The configuration files, certificates, and revocation lists are saved in the Persistant folder activated with the Personal Data feature of the Tails Persistent Volume Feature.

mkdir -p /home/amnesia/Persistent/deaddropCA/{private,newcerts,certs,usercerts,crl}  
touch /home/amnesia/Persistent/deaddropCA/index.txt  
echo '01' > /home/amnesia/Persistent/deaddropCA/serial  
echo '01' > /home/amnesia/Persistent/deaddropCA/crlnumber  
cp /etc/ssl/openssl.cnf /home/amnesia/Persistent/deaddropCA/  
cd /home/amnesia/Persistent/deaddropCA  

Edit /home/amnesia/Persistent/deaddropCA/openssl.cnf adjusting the default values

nano /home/amnesia/Persistent/deaddropCA/openssl.cnf  

dir = /home/amnesia/Persistent/deaddropCA # Where everything is kept


countryName_default = US # Replace US with your default value


stateOrProvinceName_default = NY # Replace NY with your default value


0.organizationName_default = Deaddrop # Replace Deaddrop with your default value

Update the OpenSSL environment variable to use the new config file

    export OPENSSL_CONF=/home/amnesia/Persistent/deaddropCA/openssl.cnf  

Generate the needed certificates

Generate the CA cert and revocation list. Adjust the expirations to meet your organization's policy:

openssl ecparam -name prime256v1 -genkey -out private/cakey.pem  
openssl req -x509 -extensions v3_ca -sha256 -new -key private/cakey.pem -out certs/cacert.pem -days 365  

When prompted for "YOUR name" enter a Distinguished Name for your Local CA.

openssl ca -gencrl -keyfile private/cakey.pem -cert certs/cacert.pem -out crl/cacrl.pem -crldays 365  

Generate the Journalist's Interface certs:

openssl genrsa -out private/journalist.key.pem 4096  
openssl req -sha256 -new -nodes -key private/journalist.key.pem -out newcerts/journalist.req.pem -days 365  
openssl ca -keyfile private/cakey.pem -cert certs/cacert.pem -in newcerts/journalist.req.pem -out certs/journalist.cert.pem  
openssl x509 -in certs/journalist.cert.pem -text -noout  
openssl rsa -in private/journalist.key.pem -out private/journalist.with.out.key  

Generate the user certificates for admins and journalists that will require access to the journalist interface. Convert the certs to pkcs12 format to import into browsers.

openssl genrsa -out private/first_last_name.key.pem 4096  
openssl req -sha256 -new -nodes -key private/first_last_name.key.pem -out newcerts/first_last_name.req.pem -days 365  
openssl ca -keyfile private/cakey.pem -cert certs/cacert.pem -in newcerts/first_last_name.req.pem -out usercerts/first_last_name.cert.pem  
openssl pkcs12 -export -in usercerts/first_last_name.cert.pem -inkey private/first_last_name.key.pem -out usercerts/first_last_name.p12 -name "first_last_name"  
chmod 0400 /opt/tipsCA/*/*.pem  

Copy the needed certs to the app's external harddrive

cd /opt/tips  
cp private/journalist.wo.key.pem ~/journalist_certs/  
cp crl/cacrl.pem ~/journalist_certs/  
cp certs/{cacert.pem,journalist.cert.pem} ~/journalist_certs/  

Configure Secure-Viewing-Station and Application's GPG keypair

Create Ubuntu LiveCD and prepare the SVS
Remove the hard drive containing the Local CA (after copying the generated certificates to the monitor server)
Boot from the SVS from the LiveCD

Create the Application's GPG keypair

Insert the app's secure keydrive into the SVS
Use an external hard drives rather than a external flash drives. A GPG v1 key will not work with the DeadDrop application. gnupg2 is not required to decrypt messages and files, only to create keys. Use an external entropy device when possible, if one is not available use /dev/random

Install required dependencies and create the gpg v2 keys

apt-get install gnupg2 secure-delete rng-tools -y  

Edit /etc/default/rng-tools, if you have an external entropy key use it instead of dev/random

nano /etc/default/rng-tools  

# Set to the input source for random data, leave undefined
# for the initscript to attempt auto-detection. Set to /dev/null
# for the viapadlock driver.

Start rng_tools to provide create a larger entropy source

/etc/init.d/rng-tools start  

Generate the gpg v2 keys

gpg2 --homedir  */set this to path on the secure keydrive/* --gen-key  

(1) RSA and RSA (default)
key size: 4096
real name: Journalist

Only the two selected journalist's should know the app's GPG keypair's passphrase. Follow your organization's password policy.

Export the Journalist's gpg public key

gpg2 --export --output journalist.acs --armor Journalist  

Determine and record the application's gpg key's fingerprint

gpg --homedir /var/www/deaddrop/keys --list-keys --with-fingerprint  

You will get a prompt like Command> type fpr and hit enter
it will then show you the key's fingerprint. It should look like the line below. Record it somewhere for use in the puppet nodes.pp file.


Install and configure puppet

Puppet is used to install the deaddrop application and configure the environment. Efforts were taken to apply the security hardening steps. To keep the attack surface to a minimum uninstall puppet after the environment is configured.

Monitor Server

Set the hostname if not already done

nano /etc/hostname  


hostname -F /etc/hostname  

Edit the /etc/hosts file

It should look something like below

nano /etc/hosts localhost puppet ubuntu source.domain_name source journalist.domain_name journalist monitor.domain_name monitor intvpn.domain_name intvpn intfw.domain_name intfw

Install the puppetmaster and dependencies

When promted during iptables-persistent install hit yes for the IP address version you are using. This guide uses IPv4 enter yes when prompted.

sudo apt-get install puppetmaster iptables-persistent rubygems sqlite3 libsqlite3-ruby git -y  
cd /etc/puppet/modules  
gem install puppet-module  
gem install rails -v 2.2.2   
puppet module install puppetlabs-firewall  
puppet module install puppetlabs-ntp  
puppet module install puppetlabs-vcsrepo  
puppet module install puppetlabs-apt  
puppet module install puppetlabs-git  
puppet module install puppetlabs-stdlib   
puppet module install puppetlabs-apache  

If you get a Invalid version format: 0.5.0-rc1 error then download the module manually:

tar -xzf 0.5.0-rc1.tar.gz  
mv puppetlabs-apache-0.5.0-rc1 apache  

Clone the deaddrop_puppet repo which contains the rest of the manifests and modules needed. Put them in the correct directories. These modules were not done to puppet style guide. Currently in the process of improving them and making them compliant. At some point we hope to have them hosted on puppet forge but till then use at your own risk and please help out if you are a puppet guru.

cd ~
git clone  
cp DeadDropDocs/deaddrop_puppet/manifests/* /etc/puppet/manifests/  
cp DeaddropDocs/deaddrop_puppet/modules/* /etc/puppet/modules/

Edit /etc/puppet/puppet.conf adding the following lines:

nano /etc/puppet/puppet.conf  

thin_storeconfigs = true
dbadpter = sqlite3

Gather the required files from the external harddrives

From the Secure Viewing Station's:
App's pub gpg key /etc/puppet/modules/deaddrop/files

From the Local Certificate Authority:
Journalist Interface's SSL cert /etc/puppet/modules/deaddrop/files/journalist_certs/
Journalist Interface's SSL private key /etc/puppet/modules/deaddrop/files/journalist_certs/
Local CA's root CA cert /etc/puppet/modules/deaddrop/files/journalist_certs/
Local CA's CRL list /etc/puppet/modules/deaddrop/files/journalist_certs/

Modify the default parameters

Modify parameters and hostnames the first section of nodes.pp manifest

nano /etc/puppet/manifests/nodes.pp  

node basenode {
# These values will need to be changed to reflect your environment
$domain_name = ''
$source_ip = ''
$source_hostname = 'source'
$journalist_ip = ''
$journalist_hostname = 'journalist'
$monitor_ip = ''
$monitor_hostname = 'monitor'
$admin_intVPN_ip = ''
$admin_intVPN_hostname = 'intVPN'
$journalist_intVPN_ip = ''
$journalist_intVPN_hostname = 'intVPN'
$intFWlogs_ip = ''
$intFWlogs_hostname = 'intFWlogs'
$puppetmaster_hostname = 'monitor'
$app_gpg_pub_key = 'journalist.acs'
$hmac_secret = 'use_a_random_number_generater_for_this_value'
$mailserver_ip = ''
$ossec_emailto = ''

Restart the puppetmaster

/etc/init.d/puppetmaster restart

Install Puppet on the Source and Journalist servers

apt-get install puppet iptables-persistent  

Edit /etc/hosts file to look like below: localhost ubuntu source.domain_name source journalist.domain_name journalist monitor.domain_name monitor puppet intvpn.domain_name intvpn intfw.domain_name intfw

Edit /etc/default/puppet change “START=no” to look like below

# Start puppet on boot?

Start the puppet agent on the source and journalist server

/etc/init.d/puppet restart  

Sign the puppet agent certs on the Monitor server

puppetca --list --all   
puppetca --sign --all

Run the puppet manifest to configure the environment

Run puppet on the 1) monitor server, 2) journalist interface server, 3) source interface server

puppet agent --server monitor.domain_name -t  

Steps for the system admins to create keys for Google's 2 Step Authenticator PAM module

Ensure that you are not root. Each user that needs SSH access will need to perform these steps. The same key can be used for all devices in the same environment. If the ios/android device and the servers are more than 30 seconds off the codes will not work. Currently the puppet manifest only downloads and partially install google-authenticator it does not enable it. Was worried that people may lock themselves out. You can read more about it at

Each admin should create their own code

Create the code

cd ~  


To set up you ios or android device install the 'google authenticator' app from the respective official app stores.

Open the app and click 'add key manually'

On the server run # cat ~/.google-authenticator The first line is your key. Enter that exactly into the google-authenticator app

Edit /etc/ssh/sshd_config and change ChallengeResponseAuthentication from no to yes

ChallengeResponseAuthentication yes

Edit /etc/pam.d/common-auth and add auth required so that it will look like the following

here are the per-package modules (the "Primary" block)
auth required
auth [success=1 default=ignore] nullok_secure

Restart ssh and test it in a new connection. Do not close or log out of the current window

/etc/init.d/ssh restart  

Open a new terminal window and ssh into the server and verify you can login. do not close the other window until after you verified that you still have access.

Copy you secret key to the other hosts with a command like this one

scp /home/user_name/.google-authenticator user_name@source:.  

Create a grsec patched kernel with the ubuntu-precise overlay .deb package

The grsecurity wikibook should be read thoroughly.
The steps for creating a grsec patched kernel with a ubuntu overlay were based from the following link. Please read that blog post for more information.

Gather files and packages needed for the ubuntu overlay

cd ~  
mkdir grsec  
cd grsec  
apt-get install libncurses5-dev build-essential  kernel-package git-core -y  
git clone git://  
cp -a /usr/share/kernel-package ubuntu-package  
cp ubuntu-precise/debian/control-scripts/p* ubuntu-package/pkg/image/  
cp -a /usr/share/kernel-package ubuntu-package  
cp ubuntu-precise/debian/control-scripts/p* ubuntu-package/pkg/image/  
cp ubuntu-precise/debian/control-scripts/headers-postinst ubuntu-package/pkg/headers/  

Install gcc-(version)-plugin-dev.
This package is needed by the grsec patch.

apt-get install gcc-4.6-plugin-dev -y    

Download the kernel and grsecurity patch Check the website and use the current stable version. The grsec/kernel were current at the time of writing. \“All grsecurity packages have a version string in their names. It contains both the version of the release itself and the kernel version it is meant for. For example, the version string 2.2.2- tells us that the version of this grsecurity release is 2.2.2 and it is meant for kernel version The last section of the version is a timestamp.\”


Verify the packages

gpg --import spender-gpg-key.asc
gpg --verify grsecurity-2.9.1-3.2.36-201301032034.patch.sig  
gpg --recv-keys 6092693E  
bunzip2 linux-3.2.36.tar.bz2  
gpg --verify linux-3.2.36.tar.sign  

Apply the patch to the kernel and make the grsec kernel

tar -xf linux-3.2.36.tar  
cd linux-3.2.36  
patch -p1 <../grsecurity-2.9.1-3.2.36-201301032034.patch  

Apply the old hardware config to ensure that the correct options are retained

yes "" | make oldconfig  
make menuconfig  

In the gui:

  • navigate to 'Security options'
  • navigate to 'Grsecurity'
  • enable the ‘Grsecurity’ option
  • Set ‘Configuration Method’ to ‘Automatic’
  • Set ‘Usage Type’ to ‘Server’
  • Set ‘Virtualization Type’ to ‘None’
  • Set ‘Required Priorities’ to ‘Security’
  • navigate to ‘Customize Configuration’
  • navigate to ‘Sysctl Support’ and enable ‘Sysctl support’
  • exit and save changes
make-kpkg clean  
make-kpkg --initrd --overlay-dir=../ubuntu-package kernel_image kernel_headers  

Grab a cup of coffee. When the package is complete scp the .deb files to all the servers.

Resolve PAX grub issues

apt-get install paxctl -y  
paxctl -Cpm /usr/sbin/grub-probe  
paxctl -Cpm /usr/sbin/grub-mkdevicemap  
paxctl -Cpm /usr/sbin/grub-setup  
paxctl -Cpm /usr/bin/grub-script-check  
paxctl -Cpm /usr/bin/grub-mount  

Install the grsec patched kernel

cd ..  
dpkg -i *.deb  

Review boot menu and boot into new kernel
Verify that /boot/grub/menu.lst has the correct values. Make adjustments as necessary.

sudo reboot 

After the reboot check that you booted into the correct kernel.

uname -r  

It should end in '-grsec'

After finishing installing the ensure the grsec sysctl configs are applied and locked

sysctl -p  
sysctl -w kernel.grsecurity.grsec_lock = 1  

Clean up the system and puppet firewall rules

Once the environment is verified, uninstall puppet on the puppetmaster and puppet agents to decrease the attack surface

apt-get purge rubygems puppetmaster puppet gcc make libncurses5-dev build-essential  kernel-package git-core g++ python-setuptools sqlite3 libsqlite3-ruby  

Remove the puppet rule from the monitor server in /etc/iptables/iptables_v4 file

iptables-restore < /etc/iptables/iptables_v4  

Due to Puppet bug 1737 you will need to either apply this fix linked to below or manually restrict the ssh options for www-data public key on the journalist server
Fix #1737 - ssh_authorized_keys should be able to parse options conta…

the options preceding the apache user's ssh key file should look like below: