Email-Verschlüsselung mit PGP

This chapter will introduce you to some basic concepts behind mail encryption. It is important to read to get some feeling of how mail encryption actually works and what its caveats and limitations are. PGP (Pretty Good Privacy) is the protocol we shall use for e-mail encryption. This protocol allows us to digitally sign and encrypt mail messages. It works on an end-to-end basis: messages will be encrypted on your own computer and will only be decrypted by the recipient of the message. There is no possibility for a ‘man-in-the-middle’ to decipher the contents of your encrypted message. This excludes the sub ject lines and the ‘from’ and ‘to’ addresses, which unfortunately are not encrypted in this protocol.

After having introduced these basic concepts, the next chapters will give you a handson guide to install the necessary tools on your operating system and get encryption up and running. We will focus on using Enigmail which is an extension for Thunderbird that helps you manage PGP encryption for your email. The installation process for Enigmail / PGP is difierent for Mac OSX, Windows and Ubuntu so please see the appropriate chapters in this section for instructions.

Email-Verschlüsselung mit PGP

Using a key-pair to encrypt your mail

A crucial concept in mail encryption is the usage of so-called key-pairs. A key-pair is just two separate files sitting on your harddisk or USB stick. Whenever you want to encrypt mails for a certain mail-account, you will need to have these files available to yourself in some form. If they are sitting at home on your computer, you will not be able to decrypt mail at the ofice. Putting them on a USB stick should provide a solution to this problem.
A key-pair consists of the two difierent keys: a public key and a secret key. The public key: you can give this key to other people, so they can send you encrypted mails. This file does not have to be kept secret. The secret key: this basically is your secret file to decrypt emails people send to you. It should never be given to someone else.

Sending encrypted mails to other people: you need their public key

I have five colleagues at work and I want to send encrypted mails to them. I need to have public keys for each of their addresses. They can send me these keys using ordinary mail, or they can give them to me in person, or put them on a USB stick, or they can have their keys on a website. It doesn’t matter, as long as I can trust those keys really belong to the person I want to correspond with. My software puts the keys on my ‘keyring’, so my mail application knows how to send them encrypted mails.

Receiving encrypted mails from other people: they need my public key

For my five (or thirty) colleagues to be able to send me encrypted mails, the process goes the other way around. I need to distribute my public key to each of them.
Conclusion: encryption requires public key distribution!

Installing PGP on Windows

To complicate matters a little -PGP is the protocol used for encrypting e-mail by various softwares. To get PGP to work with Thunderbird we need to install GPG -a free software implementation of PGP and Enigmail -an extension of Thunderbird that allows you to use GPG. . . Confusedfi! Don’t worry about it, all you have to know is how to encrypt your email with PGP and you need to install both GPG and Enigmail. Here is how to do it. . .

Installing PGP (GPG) on Microsoft Windows

The GNU Privacy Guard (GnuPG) is software which is required to send PGP encrypted or signed emails. It is necessary to install this software before being able to do any encryption.

Head to the website of the Gpg4win pro ject. Go to http://gpg4win.org/

On the left side of the website, you will find a ‘Download’ link. Click on it.

Email-Verschlüsselung mit PGP

This will take you to a page where you can download the Gpg4Win. Click on the button which ofiers you the latest stable version (not beta) of Gpg4Win.

Email-Verschlüsselung mit PGP

This will download you an .exe file. Depending on your browser, you may have to double-click on this downloaded file (which will be called something like gpg4qin-2.1.0.exe) before something happens. Windows will ask you if you are sure you want to install this program. Answer yes.

Then complete the installation by agreeing to the license, choosing appropriate language and accepting the default options by clicking ‘Next’, unless you have a particular reason not to.

The installer will ask you where to put the application on your computer. The default setting should be fine but make a note of it as we may need this later. Click on ‘Next’ when you agree.

Installing with the Enigmail extension

After you have successfully installed the PGP software as we described above you are now ready to install the Enigmail add-on. Enigmail is a Thunderbird add-on that lets you protect the privacy of your email conversations. Enigmail is simply an interface that lets you use PGP encryption from within Thunderbird. Enigmail is based on public-key cryptography. In this method, each individual must generate her/his own personal key pair. The first key is known as the private key. It is protected by a password or passphrase, guarded and never shared with anyone. The second key is known as the public key. This key can be shared with any of your correspondents. Once you have a correspondent’s public key you can begin sending encrypted e-mails to this person. Only she will be able to decrypt and read your emails, because she is the only person who has access to the matching private key. Similarly, if you send a copy of your own public key to your e-mail contacts and keep the matching private key secret, only you will be able to read encrypted messages from those contacts.

Enigmail also lets you attach digital signatures to your messages. The recipient of your message who has a genuine copy of your public key will be able to verify that the e-mail comes from you, and that its content was not tampered with on the way. Similarly, if you have a correspondent’s public key, you can verify the digital signatures on her messages.

Installation steps

To begin installing Enigmail, perform the following steps:

1. Open Thunderbird, then Select Tools > Add-ons to activate the Add-ons window; the Add-ons window will appear with the default Get Add-ons pane enabled.

2. Enter enigmail in the search bar, like below, and click on the search icon.

3. Simply click on the ‘Add to Thunderbird’ button to start the installation.

4. Thunderbird will ask you if you are certain you want to install this add-on. We trust this application so we should click on the ‘Install now’ button.

5. After some time the installation should be completed and the following window should appear. Please click on the ‘Restart Thunderbird’ button.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

 Installing PGP on Ubuntu

We will use the Ubuntu Software Centre for installing PGP (Enigmail and accessories). First open the Ubuntu Software Center through the Unity menu by typing ‘software’ into the Unity search area

Email-Verschlüsselung mit PGP

Click on the ‘Ubuntu Software Center’.

Type into the search field ‘Enigmail’ and search results should be returned automatically:

Highlight the Enigmail item (it should be highlighted by default) and click ‘Install’ and you will be asked to authenticate the installation process.

Enter your password and click ‘Authenticate’. The installation process will begin.

When the process is completed you get very little feedback from Ubuntu. The progress bar at the top left disappears. The ‘In Progress’ text on the right also disappears. Enigmail should now be installed.

Email-Verschlüsselung mit PGP

Installing PGP on OSX

The GNU Privacy Guard (GnuPG) is software which enables you to send PGP encrypted or signed emails. It is necessary to install this software before being able to do any encryption. This chapter covers the installation steps required to install GnuPG on Mac OSX.

Getting started

For this chapter we assume you have the latest version of:

  • OSX installed (10.6.7)
  • Thunderbird (3.1.10)

Note on OSX Mail: It is possible to use PGP with the build-in mail program of OSX. But we do not recommend this because this option relies on a hack of the program which is neither open or supported by its developer and breaks with every update of the mail program. So unless you really have no other option we advice you to switch to Mozilla Thunderbird as your default mail program if you want to use PGP.

Downloading and installing the Software

1. For OSX there is a bundle available which will install everything you need in one in stallation. You can get it by directing your browser to http://www.gpgtools.org/ and clicking on the big blue disk with “Download GPGTools Installer” written under it. It will redirect you to another page on http://www.gpgtools.org/installer/index.html where you can actually download the software.

(nb. We are using the latest version Firefox for this manual, so the screens might look a little bit difierent if you are using a difierent browser)

2. Download the software by choosing ‘Save File’ and clicking ‘OK’ in the dialogue.

3. Navigate to the folder where you normally store your downloads (Mostly the desktop or the downloads folder surprisingly) en double click the ’.DMG’ file to open the virtual disk containing the installer.

4. Open the installer by double-clicking on the icon.

5. The program will check your computer to see if it can run on the computer.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

(Note, if you’re Mac is bought before 2006 it will not have an intel processor required to run this software and the installation will fail. Sadly it is beyond the scope op this manual to also take into account computers over five year old)

You will be guided by the program through the next steps like accepting the license agreement. But stop pressing all the OK’s and Agrees as soon as you come to the ‘Installation Type’ screen:

6. Clicking ‘Customize’ will open this screen where you several options of programs and software to install. You can click on each one of them to get a little bit of information on what is is, what it does and why you might need it.

Email-Verschlüsselung mit PGP

As said in the intro; we advise against using Apple Mail in combination with PGP. Therefore you won’t be needing ‘GPGMail’, as this enables PGP on Apple Mail, and you can uncheck it.

‘Enigmail’ on the other hand is very important as it is the component that will enable Thunderbird to use PGP. In the screen shot here it is greyed out as the installer wasn’t
able to identify my installation of Thunderbird. Since this seems to be a bug. You can also install Enigmail from within Thunderbird as is explained in another chapter. If the option is not greyed out in your installation, you should tick it.

After you checked all the components you want to install click ‘Install’ to proceed. The installer will ask you for your password and after you enter that the installation will run and complete; Hooray!

Email-Verschlüsselung mit PGP

Installing up Engimail

1. Open Thunderbird, then Select Tools > Add-ons to activate the Add-ons window; the Add-ons window will appear with the default Get Add-ons pane enabled.
In the Add-On window, you can search for ‘Enigmail’ and install the extension by clicking ‘Add to Thunderbird . . . ’

2. After you open the Add-On window, you can search for ‘Enigmail’ and install the extension by clicking ‘Add to Thunderbird . . . ’

3. Click on ‘Install Now’ to download and install the extension.

Be aware that you will have to restart Thunderbird to use the functionality of this extension!

Now that you have successfully downloaded and installed Enigmail and PGP you can go on to the Chapter that deals with setting up the software for use.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Installing GPG on Android

With the growing usage of mobile phones for e-mail, it’s interesting to be able to use GPG also on your mobile. This way you can still read the messages sent to you in GPG on your phone and not only on your computer.

Install the Android Privacy Guard (APG) and K-9 Mail applications to your Android device from the Google Play Store or another trusted source.

1. Generate a new private key that uses DSA-Elgamal with your PC’s GPG installation (You can only create keys with up to 1024bit key length on Android itself ).

2. Copy the private key to your Android device.

3. Import the private key to APG. You may wish to have APG automatically delete the plaintext copy of your private key from your Android device’s filesystem.

4. Set-up your e-mail accounts in K-9 Mail.

5. In the settings for each account, under Cryptography, make sure that K-9 Mail knows to use APG. You can also find options here to make K-9 Mail automatically sign your messages and/or encrypt them if APG can find a public key for the recipient(s).

6. Try it out.

APG

This is a small tool which makes GPG encryption possible on the phone. You can use APG to manage your private and public keys. The options in the application are quite straightforward if you are a little knowledge of GPG in general.

Management of keys is not very well implemented yet. The best way is to manually copy all your public keys to the SD card in the APG folder. Then it’s easy to import your keys. After you’ve imported your public and private keys, GPG encrypting, signing and decrypting will be available for other applications as long as these applications have integrated encryption/GPG.

GPG enabled e-mail on Android: K-9 Mail

The default mail application does not support GPG. Luckily there is an excellent alternative: K-9 Mail. This application is based on the original Android mail application but with some improvements. The application can use APG as it’s GPG provider. Setting up K-9 Mail is straightforward and similar to setting up mail in the Android default mail application. In the settings menu there is an option to enable “Cryptography” for GPG mail signing.

If you want to access your GPG mails on your phone this application is a must have.

Please note, due to some small bugs in K-9 Mail and/or APG, it’s very advisable to disable HTML mail and use only Plain text. HTML mails are not encrypted nicely and are often not readable.

Enigmail comes with a nice wizard to help you create a public/private key pair (see the chapter introducing PGP for an explanation). You can start the wizard at any time within Thunderbird by selecting OpenPGP > Setup Wizard from the menu on top.

1. This is what the wizard looks like. Please read the text on every window carefully.
It provides useful information and helps you setup PGP to your personal preferences. In the first screen, click on Next to start the configuration.

2. The wizard asks you whether you want to sign all your outgoing mail messages. Signing all your messages is a good choice. If you choose not to, you can still manually

Email-Verschlüsselung mit PGP

Figure 7.20: GPG Keys

decide to sign a message when you are composing it. Click on the ‘Next’ button after you have made a decision.

Email-Verschlüsselung mit PGP

3. On the following screen, the wizard asks you whether you want to encrypt all your outgoing mail messages. Unlike signing of mails, encryption requires the recipient to have PGP software installed. You should probably answer ‘no’ to this question, so that you will send normal (unencrypted) mail by default. After you have made your decision, click on the ‘Next’ button.

4. On the following screen the wizard asks if it can change some of your mail formatting settings to better work with PGP. It is a good choice to answer ‘Yes’ here. This will

Email-Verschlüsselung mit PGP

Webmail and PGP

The only safe way of encrypting email inside of the browser window is to encypt it outside and then copy & paste the encrypted text into the browser window. For example, write the text in a text editor like gedit, vim or kate and save it as .txt file (in this example “message.txt”. Then type gpg -ase -r the.recipients.email.address@or.gpg.id -r your.gpg.id message.txt A new file called “message.asc” will be created. It contains the encrypted message and can thus be either attached to an email or its content safely copy & pasted into the browser window. To decrypt a message from the browser window, simply type gpg into the command line and hit Enter. Then copy & paste the message to be decrpyted into the commandline window and after being asked for your passphrase hit Ctrl+D (this enters a end-of-file character and prompts gpg to output the cleartext message). If using the commandline seems too cumbersome to you, you might consider installing a helper application like gpgApplet, kgpg or whatever application ships with your operating system. mean that by default, mail will be composed in plain text rather than HTML. Click on the ‘Next’ button after you have made your decision.

Email-Verschlüsselung mit PGP

5. In the following screen, select one of your mail accounts; the default is selected for you if you only have one. In the ‘Passphrase’ text box you must enter a password. This is a new password which is used to protect your private key. It is very important to remember this password, because you cannot read your own encrypted emails if you forget it. Make it a strong password, ideally 20 characters or longer. Please see the chapter on passwords for help on creating unique, long and easy to remember passwords. After you have selected your account and created a passphrase, click on the ‘Next’ button.

Email-Verschlüsselung mit PGP

6. In the following screen the wizard summarizes the actions it will take to enable PGP encryption for your account. If you are satisfied, click the ‘Next’ button.
7. Your keys will be created by the wizard, which will take some time. When completed, click on the ‘Next’ button.
8. You now have your own PGP key-pair. The wizard will ask you if you also want to create a ‘Revocation certificate’. This is a file which can be used to inform everyone if your private key is compromised, for example if your laptop is stolen. Think of it as a ‘kill switch’ for your PGP identity. You may also wish to revoke the key simply because you have generated a new one, and the old one is obsolete.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

9. If you decided to generate a revocation certificate, the wizard will ask you where the file should be saved. The dialog will look difierent depending on which operating system you use. It is a good idea to rename the file to something sensible like my revocation certificate. Click on ‘Save’ when you you have decided on a location.

10. If you decided to generate a revocation certificate, the wizard informs you it has been successfully stored. You may want to print it out or burn it to a CD and keep it in a safe place.

11. The wizard will inform you it has completed.

Email-Verschlüsselung mit PGP

Figure 7.28: GPG Keys

Email-Verschlüsselung mit PGP

Congratulations, you now have a fully PGP-configured mail client. In the next chapter we will explain how to manage your keys, sign messages and do encryption. Thunderbird can help you do a lot of these things automatically.

Email-Verschlüsselung mit PGP

Daily PGP usage

In the previous chapters we have have explained how to set up a secure mail environment using Thunderbird, GPG and Enigmail. We assume you have installed the software and have successfully followed the wizard instructions to generate an encryption key-pair as described in the previous chapter. This chapter will describe how to use your secured Thunderbird in daily life to protect your e-mail communication. In particular we will focus on:

1. Encrypting attachments

2. Entering your pass-phrase

3. Receiving encrypted e-mail

4. Sending and receiving public keys

5. Receiving public keys and adding them to your key ring

6. Using public key servers

7. Signing e-mails to an individual

8. Sending encrypted e-mails to an individual

9. Automating encryption to certain recipients

10. Verifying incoming e-mails

11. Revoking your GPG key pair

12. What to do when you have lost your secret key, or forgot your passphrase

13. What to do when your secret key has been stolen, or compromised

14. Backing up your keys

First we shall explain two dialog windows that will inevitably appear after you start using Thunderbird to encrypt your emails.

Encrypting attachments

The dialog window below will pop-up whenever you are sending an encrypted email with attachments for the first time. Thunderbird asks a technical question on how to encrypt attachments to your mail. The second (default) option is the best choice, because it combines security with the highest compatibility. You should also select the ‘Use the selected method for all future attachments’ option. Then click ‘OK’ and your mail should be sent with no further delay.

Email-Verschlüsselung mit PGP

Entering your pass-phrase

For security reasons, the pass-phrase to your secret key is stored temporarily in memory. Every now and then the dialog window below will pop-up. Thunderbird asks you for the pass-phrase to your secret key. This should be difierent from your normal email password. It was the pass-phrase you have entered when creating your key-pair in the previous chapter. Enter the pass-phrase in the text-box and click on ‘OK’

Email-Verschlüsselung mit PGP

Receiving encrypted e-mails

The decryption of e-mails is handled automatically by Enigmail, the only action that may be needed on your behalf is to enter the pass-phrase to your secret key. However, in order to have any kind of encrypted correspondence with somebody, you will first need to exchange public keys.

Sending and receiving public keys

There are multiple ways to distribute your public key to friends or colleagues. By far the simplest way is to attach the key to a mail. In order for your friend to be able to trust that the message actually came from you, you should inform them in person (if possible) and also require them to reply to your mail. This should at least prevent easy forgeries. You have to decide for yourself what level of validation is necessary. This is also true when receiving emails from third-parties containing public keys. Contact your correspondent through some means of communication other than e-mail. You can use a telephone, text messages, Voice over Internet Protocol (VoIP) or any other method, but you must be absolutely certain that you are really talking to the right person. As a result, telephone conversations and face-to-face meetings work best, if they are convenient and if they can be arranged safely.

Sending your public key is easy.

1. In Thunderbird, click on the „send“ button.

2. Compose a mail to your friend or colleague and tell them you are sending them your PGP public key. If your friend does not know what that means, you may have to explain them and point them to this documentation.

3. Before actually sending the mail, click to OpenPGP > Attach My Public Key option on the menu bar of the mail compose window. Next to this option a marked sign will appear. See the example below.

4. Send your mail by clicking on the

Email-Verschlüsselung mit PGP
Receiving public keys and adding them to your keyring

Lets say we receive a public key from a friend by mail. The key will show up in Thunderbird as an attached file. Scroll down the message and below you will find tabs with one or two file names. The extension of this public key file will be .asc, difierent from the extension of an attached GPG signature, which ends with .asc.sig Look at the example email in the next image, which is a received, signed GPG message containing an attached public key. We notice a yellow bar with a warning message: ‘OpenPGP: Unverified signature, click on ’Details’ button for more information’. Thunderbird warns us that the sender is not known yet, which is correct. This will change once we have accepted the public key. What are all those strange characters doing in the mail messagefi Because Thunderbird does not yet recognize the signature as valid, it prints out the entire raw signature, just as it has received it. This is how digitally signed GPG messages will appear to those recipients who do not have your public key. The most important thing in this example is to find the attached GPG public key. We mentioned it is a file that ends with .asc. In this example it’s the first attachment on the left, in the red circle. Double-clicking on this attachment will make Thunderbird recognize the key.

Email-Verschlüsselung mit PGP

After we have clicked on the attachment, the following pop-up will appear. Thunderbird has recognized the GPG public key file. Click on ‘Import’ to add this key to your keyring. The following pop-up should appear. Thunderbird says the operation was successful. Click on ‘OK’ and you are almost done.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

We are back in the main Thunderbird screen and we refresh the view on this particular example message, by clicking on some other message and back for example. Now the body of the message looks difierent (see below). This time Thunderbird does recognize the signature, because we have added the public key of the sender. There is still one thing that remains. While Thunderbird now recognizes the signature, we should explicitly trust that the public key really belongs to the sender in real life. We realize this when we take a closer look at the green bar (see below). While the signature is good, it is still UNTRUSTED. We will now decide to trust this particular public key and the signatures made by it. We can do this immediately by clicking on ‘Details’. A small menu will appear (see below). From this menu we should click on the option ‘Sign Sender’s Key . . . ’.

After we have selected ‘Sign Sender’s Key . . . ’ we will get another selection window (see below). We are requested to state how carefully we have checked this key for validity. The explanation of levels of trust and trust networks in GPG falls outside the scope of this document. We will not use this information, therefore we will just select the option ‘I will not answer’. Also select the option ‘Local signature (cannot be exported)’. Click on the ‘OK’ button to finishing signing this key. This finishes accepting the public key. You can now send encrypted mail to this individual.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Using public key servers

Another method of distributing public keys is by putting them on a public key server. This allows anyone to check whether your email address has GPG support, and then download your public key.

To put your own key on a keyserver, take the following steps.

1. Head to the key manager by using the Thunderbird menu and click on OpenPGP > Key Management

2. The key management window will be displayed and looks like this:

3. You need to have selected the ‘Display All Keys by Default’ option to get a list of all your keys. Look up your own email address in the list and right click on the address. A selection window will appear with some options. Select the option ‘Upload Public Keys to Keyserver’.

4. You will see a small dialog window like below. The default server to distribute your keys to is good. Press ’OK” and distribute your public key to the world.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

To look up whether some email address has a public key available on a server, take the following steps.

1. Head to the key manager by using the Thunderbird menu and click on OpenPGP > Key Management

2. In the key manager window menu bar, select Keyserver > Search for Keys

3. In this example we will look-up up the key for the creator of PGP software, Philip Zimmermann. After we have entered the email address, we click on ‘OK’.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

4. The next window displays the result of our search. We have found the public key. It is automatically selected. Just click on ‘OK’ to import the key.

5. Importing the key will take some time. On completion you should see a pop-up window like below.

6. The final step is to locally sign this key, to indicate that we trust it. When you are back in the key manager, make sure you have selected the ‘Display All Keys by Default’ option. You should now see the newly imported key in the list. Right-click on the address and select the option ‘Sign Key’ from the list.

7. Select the options ‘I will not answer’ and ‘Local signature (cannot be exported)’, then click on ‘OK’. You are now finished and can send Philip Zimmermann encrypted mail.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Signing emails to an individual

Digitally signing email messages is a way to prove to recipients that you are the actual sender of a mail message. Those recipients who have received your public key will be able to verify that your message is authentic.

1. Ofier your friend your public key, using the method described earlier in this chapter.

2. In Thunderbird, click on the

3. Before actually sending the mail, enable the OpenPGP > Sign Message option via the menu bar of the mail compose window, if it is not enable already. Once you have enabled this option, by clicking on it, a marked sign will appear. Clicking again should disable encryption again. See the example below.

4. Click on the Email-Verschlüsselung mit PGPicon.Email-Verschlüsselung mit PGP button and your signed mail will be sent.

Email-Verschlüsselung mit PGP

1. You should have received the public key from the friend or colleague you want to email and you should have accepted their public key, using the method describe earlier in this chapter.

2. In Thunderbird, click on the

3. Compose a mail to the friend or colleague, from who you have previously received their public key. Remember the sub ject line of the message will not be encrypted, only the message body itself, and any attachments.

4. Before actually sending the mail, enable the OpenPGP > Encrypt Message option via the menu bar of the mail compose window, if it is not enabled already. Once you have enabled this option, by clicking on it, a marked sign will appear. Clicking again should disable encryption again. See the example below.

Email-Verschlüsselung mit PGP

5. Click on the“send“ button and your encrypted mail will be sent.

Automating encryption to certain recipients

You will often want to make sure all your messages to a certain colleague or friend are signed and encrypted. This is good practice, because you may forget to enable the encryption manually. You can do this by editing the per-recipient rules. To do this we access the OpenPGP per-recipient rule editor.

Select OpenPGP > Preferences from the Thunderbird menu bar.

Email-Verschlüsselung mit PGP

The preferences window will appear like below. We need to click on ‘Display Expert Settings’. New menu tabs will appear in the window. Go to the tab ‘Key Selection’ and then click on the button labeled ‘Edit Rules . . . ’ We are now shown the per-recipient rules editor (see below). This editor can be used to specify the way how messages to certain recipients are sent. We will now add a rule saying we want to encrypt and sign all mail messages to maildemo@greenhost.nl

First click on the ‘Add’ button. Now the window to add a new rule will be shown. The first thing we should enter is the email address of the recipient. In the example below we have entered maildemo@greenhost.nl

Now we will set the encryption defaults by using the drop-downs below. For Signing select ‘Always’. For Encryption also select ‘Always’.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Finally we have to select the public key of the recipient, with which to encrypt our messages. Do not forget this important step, otherwise the e-mail will not be encrypted. Click on the button labeled ‘Select Key(s). . . ’. The key selection window will show up. The most obvious key will be selected by default. In the example below, we only have one public key available. We can select keys by clicking on the small box next to the address. Then we click ‘OK’ and close all relevant windows and we are finished.

Email-Verschlüsselung mit PGP

Verifying incoming e-mails

Decrypting email messages sent to you will be fully automatic and transparent. But it is obviously important to see whether or not a message to you has in fact been encrypted or signed. This information is available by looking at the special bar above the message body.

A valid signature will be recognized by a green bar above the mail message like the example image below.

Email-Verschlüsselung mit PGP

The last example message was signed but not encrypted. If the message had been encrypted, it would show like this:

When a message which has been encrypted, but not signed, it could have been a forgery by someone. The status bar will become gray like in the image below and

Email-Verschlüsselung mit PGP

tells you that while the message was sent securely (encrypted), the sender could have been someone else than the person behind the email address you will see in the ‘From’ header. The signature is neccessaty to verify the real sender of the message. Of course it is perfectly possible that you have published your public key on the Internet and you allow people to send you emails anonymously. But is it also possible that someone is trying to impersonate one of your friends.

Email-Verschlüsselung mit PGP

Similarly if you receive a signed email from somebody you know, and you have this persons public key, but still the status bar becomes yellow and displays a warning message, it is likely that someone is attempting to send you forged emails!

Email-Verschlüsselung mit PGP

Sometimes secret keys get stolen or lost. The owner of the key will inform his friends and send them a so-called revocation certificate (more explanation of this in the next paragraph). Revocation means that we no longer trust the old key. The thief may afterwards still try his luck and send you a falsely signed mail message. The status bar will now look like this: Strangely enough Thunderbird in this situation will still display a green status bar! It is important to look at the contents of the status bar in order to understand the encryption aspects of a message. GPG allows for strong security and privacy, but only if you are familiar with its use and concepts. Pay attention to warnings in the status bar.

Email-Verschlüsselung mit PGP

Revoking your GPG key-pair

Your secret key has been stolen by somebody. Your harddisk crashed and you have lost all your data. If your key is lost, you can no longer decrypt messages. If your key has been stolen, somebody else can decrypt your communication. You need to make a new set of keys. The process of creating keys, using the OpenPGP wizard in Thunderbird, has been described in this manual. But first you want to tell the world that your old public key is now worthless, or even dangerous to use.

What to do when you have lost your secret key, or forgot your passphrase

During the creation of your key-pair, the OpenPGP wizard ofiered you the possibility to create a so-called revocation certificate. This is a special file you send to others in the advent you have to disable your key. If you have a copy of this file, sending the revocation key is simply sending the file as an attachment to all your friends. You can no longer send signed mails (obviously, because you have lost your secret key). That doesn’t matter. Send it as a normal mail. The revocation certificate file could only have been created by the owner of the secret key and proves he or she wants to revoke it. That’s why it should normally be kept hidden from others.If you do not have the revocation certificate, there exists no other option than for you to contact your friends personally and convince them your key is lost and that they should no longer trust it.

What to do when your secret key has been stolen, or compromised

If you have reason to believe your secret key has been compromised, or worse your secret key and passphrase, it is very important to contact others that they should stop sending you encrypted messages. With your secret key, other persons will be able to break the encryption of your e-mail messages if they also have your passphrase. This is also true for those messages you have send in the past. Cracking the passphrase is not trivial, but it may be possible if the party has lots of resources, like a state or a big organization for example, or if your passphrase is too weak. In any case you should assume the worst and assume your passphrase may have been compromised. Send a revocation certificate file to all your friends or contact them personally and inform them of the situation.

Even after you have revoked your old key pair, the stolen key may still be used to decrypt your previous correspondence. You should consider other ways to protect that old correspondence, for instance by re-encrypting it with a new key. The latter operation will not be discussed in this manual. If you are uncertain you should seek assistance from experts or look up more information on the web.

Receiving a revocation certificate

If one of your friends sends you a revocation certificate, s/he asks you to distrust his public key from now on. You should always accept such a request and ‘import’ the certificate to disable their key. The process of accepting a revocation certificate is exactly the same as accepting a public key, as has already been described in the chapter. Thunderbird will ask you if you want to import the ‘OpenPGP key file’. Once you have done so, a confirmation pop-up should be displayed like below.

Email-Verschlüsselung mit PGP

Preparing for the worst: backup your keys

Your keys are usually stored on your hard disk as normal files. They may get lost if your computer gets damaged. It is strongly advised to keep a backup of your keys in a safe place, like a vault. Making a a backup of your secret key has another security advantage as well. Whenever you fear your laptop or computer is in immediate danger of being confiscated, you can safely delete your key-pair. Your email will be rendered unreadable immediately. At a later stage, you can retrieve your keys from the vault and re-import them in Thunderbird. To make a backup of your key-pair, first head to the key manager by using the Thunderbird menu and click on OpenPGP > Key Management. You need to have selected the ‘Display All Keys by Default’ option to get a list of all your keys. Lookup your own email address in the list and right click on the address. A selection window will appear with some options. Select the option ‘Export Keys to File’. Now we will save the key-pair to a file. Thunderbird asks us if we want to include the secret key as well. We do want to include the secret key, therefore we select ‘Export Secret Keys’. Finally Thunderbird asks us for the location of the key file. You can store the file anywhere you like, network disk, USB-stick. Just remember to hide it away from other people.

Email-Verschlüsselung mit PGP

Email-Verschlüsselung mit PGP

Further reading

More documentation on using GPG with Thunderbird can be found on the website of the Enigmail plugin. The Enigmail handbook is the guide you will want to use.
http://enigmail.mozdev.org/documentation/handbook.php.html