Microsoft Outlook

First, go to the downloads page and click the link for the “Microsoft Outlook” add-in. Run the executable and continue through the installation process. If you are prompted to download and install the Visual Studio 2010 Tools for Office Runtime, go ahead and do so. In Outlook 2007, you should see an “enMailing” menu at the top of the window, with an “Options” menu item:

Outlook Menu

In later versions of Outlook with the ribbon interface, you should see an “Add-Ins” ribbon with an “enMailing” section that has an “Options” button. I don’t have a later version of Outlook, so I can’t verify that. Click “Options” under enMailing, and the following dialog will pop up:

Firefox Settings

Enter your enMailing username and password. Also specify a name for this device. It’s a good idea to use a name that you will be able to recognize in the future, such as “Outlook (home)” or “Outlook (work).” Giving a descriptive name will make it easier for you to de-authorize the device in the future should you ever want to. After entering your username, password, and the device name, click “Authenticate.” If your username and password were correct, Outlook will become an authorized device:

Outlook Settings Authorized

The “Group” setting allows you to set the default group for which you will encrypt messages. This is easy to change later, but you can change it now if you want to. Click “OK.” You are now ready to encrypt and decrypt messages in Outlook. In the compose message window, you will see an “Add-Ins” ribbon with an “enMailing” section:

Outlook Compose Ribbon

The “Encrypt on Send” button is a toggle that tells Outlook whether to encrypt your entire message before sending. The “Group” drop down box allows you to select the group for which to encrypt the message. The “Decrypt” button allows you to decrypt your message if you’ve partially encrypted it. The “Options” button opens the enMailing settings window (where you just were).

To encrypt your entire message, just toggle the “Encrypt on Send” button, type your message, and send away. Keep in mind that all encryption is done for the currently selected group. If you want to encrypt for a different group, select the group before sending the message. Unfortunately, there isn’t a way to encrypt only parts of messages in Outlook. This is due to the limitations inherent in Outlook add-ins, unfortunately.

Reading encrypted messages that you receive is easy. When you receive an encrypted message, you will see that your Outlook reading pane (or individual message window if you open the message in its own window) splits in two:

Outlook Reading Pane

The top part of the window displays the message encrypted. The bottom half of the window displays the message decrypted by enMailing. When viewing messages without encryptions, the bottom “enMailing” pane will be hidden and Outlook will function normally. You only get this split view when viewing messages decrypted by enMailing.

When you reply to an enMailing encrypted message, you will see the decrypted message in the compose window. The option to encrypt the message when you send it will also be enabled by default.