How to Install & Use GnuPG on Entourage
- 1). Install the freely available "GPGTools" package designed for the Mac operating system. The software may be downloaded from the official website (see Resources) and includes the GPG Keyring utility, as well the latest version of the GPG encryption application for the Mac. The package is in the form of an Apple .dmg file, and the installation should begin immediately upon clicking the link. Allow the entire package to complete the installation process before proceeding to the following step.
- 2). Close the Entourage email program if it is currently running on your Apple computer, then open your web browser to navigate to the EntourageGPG website where you can download the most recent version of EntourageGPG (see Resources). EntourageGPG is a separate program from GPGTools, and provides an interface within Entourage to make use of the GPG software and utilities in GPGTools. Click the "Download Now" link at the top of the page. On the resulting page, click on the link titled "EntourageGPG," which will appear in blue text. Finally, on the last page, click on the latest version, which will appear at the far top of the list of versions.
- 3). Decompress the downloaded EntourageGPG package you downloaded, then double-click on the .dmg file to begin the installation process. When asked if you desire for all of the tools to be installed, click "Yes." Wait until the software has finished installing before continuing to the next step.
- 4). Browse through your installed programs and locate the GPG Keyring Management Utility that was installed as part of the GPGTools package. This utility allows you to generate your encryption key pair, as well as to add and manage the public keys of your friends, relatives and others who may be using GPG encryption. Click on the Keyring Management Utility to start it, then click the "Key" menu in the top navigation panel. In the list of selections, click on "Generate" to begin generating your key pair. The key pair will include a password-protected private key that is only to remain on your computer, and also a public key that is to be sent to your recipients for addition to their own GPG keyrings. Enter the email address you will be using with EntourageGPG when asked to provide it. It is safe to accept all the rest of the settings as their defaults. Wait for the key pair to be completed before continuing with the following step.
- 5). Use the Keyring Manager Utility to export a copy of your public key onto your hard drive. Once it has been exported, send the public key as an email attachment to your friends, relatives or business associates who may also be using GPG encryption. In the email, ask them to send you an exported copy of their keys as well. Once you receive emails with their keys, click on them so the Keyring Manager automatically starts. When asked if you desire to import the public key and to add it to your keyring, click "Yes."
- 6). Start your Entourage email program. Once the program is running, you will notice a new script menu for EntourageGPG within the navigation panel of the email program. When you are finished completing any email that will be sent to a recipient who is also using GPG, click on the script menu and choose which operation you desire to be applied to your message before it is sent. Menu options include: "Decrypt or Verify," "Sign," "Encrypt and Sign," "Encrypt" and "Symmetric Encrypt." The most common use is to use "Decrypt or Verify" for incoming messages that are encrypted, and "Encrypt and Sign" for any messages you are sending.
- 7). Type in the passphrase (password protection for your private key) when asked to do so after clicking "Send" to send your email. The passphrase must be the same one you used when you created your key pair within the GPG Keyring Manager Utility. At this point your email will be sent in its encrypted form to your designated recipient. If you added the recipient's key to your keyring, it will use that recipient's public key along with your private key for encryption of the email, making it readable only by that recipient.
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