Encrypting your Entourage Database

Entourage keeps your mail in a set of files (most significantly, one named Database) in your OS X user home folder's Documents/Microsoft User Data/Office X Identities/Main Identity folder. (The name "Main Identity" is the default; other identities are possible.)

To prevent others from accessing the mail, address book, calendar and notes stored in that folder, you can relocate that data into an OS X encrypted disk image. The process for doing so isn't terribly complicated.

Before doing anything, you should back up the Office X Identities folder. Just in case something goes wrong, you will want to retrieve your mail. And it's a good idea to regularly backup that folder, anyway. A good backup forgives a lot of mistakes.

Also before starting, you will want to quit all Office X applications. Then use the Activity Monitor to quit the "Microsoft Database daemon". This process uses the Entourage database and will really confuse things if it is left running.

Next, you'll use the OS X Disk Utility to make a blank encrypted disk image (with plenty of extra space for your Entourage database to grow!) Copy the "Main Identity" folder into the encrypted disk image. Remove the old "Main Identity" folder and replace it with an alias to the copy of the "Main Identity" folder on the encrypted disk image.

From then on, every time you start Entourage it will need to mount that encrypted disk image (either getting the password from your keychain or prompting you for it, depending on whether you store the password on the keychain.)

Do not forget this password. If you forget the password, you will not be able to get at your mail. There's no trick to bypass that. No password, no mail.

For those who want more detail about that procedure, here it is:

Make a backup of your OS X user Home folder's Documents/Microsoft User Data/Office X Identities/Main Identity folder. (The name "Main Identity" is the default; other identities are possible.)
Quit all Office applications. Entourage, of course. But also Word, Excel, Power Point. Believe it not, all these applications use the database daemon which uses the Entourage identity we're going to be encrypting.
Launch OS X's Activity Monitor (you'll find in/Applications/Utilities).
Locate the "Database Daemon" process. Select it. Then click "Quit process" and confirm that you want to Quit the application.
Locate the " Main identity" folder in Finder and select "Get info" from the file menu.
Make a note of the folder's size.
When you create the encrypted disk image, you will want to make it considerably larger than the current size of your current "Main identity" folder. This will allow you to receive more mail and add more contacts and appointments. You'll also want to have enough room so Entourage can compact or rebuild the database, which will require at least twice the current size. If you have a mature database, I suggest making it three times the current size. If you are just starting with Entourage, I suggest you make even larger!
Launch OS X's Disk Utility (you'll find in/Applications/Utilities).
Click the " New image" icon. Give the disk image a name (E.g. EncryptedMail) and a place to store it. I keep mine in the "Office X identities" folder, but any place convenient will do.
Set "Encryption:" to AES-128.
Set "Size:" to "Custom"; you'll be prompted for the size you want. Make it considerably larger than the current size of your current "Main identity" folder. I suggest making it at least three times the current "Main Identity" size. This will allow you to grow and have enough room so Entourage can compact or rebuild the database. If you are too stingy, eventually the disk image will become full (Entourage will give you a nasty error message) and you will have to create a new, larger image and transfer your data into it.
Click "Create". You'll be prompted for a Password.
Pick a nontrivial password, so it won't be easily guessed. Do not forget this password. If you forget the password, you will not be able to get at your mail. There's no trick to bypass that. No password, no mail.
You can choose to put the password on your keychain. If you do, then the image can open automatically whenever your keychain is unlocked. This is a way to avoid for getting your password, but if you walk away and leave your keychain open, others may be able to see your mail.
Return to the Finder and copy your "Main identity" folder into the encrypted disk image you just created.
Trash the old "Main identity" folder. (You made a backup, right?)
Make an alias for the "Main Identity" folder in the encrypted disk image and move it into the "Office X Identities" folder where the "Main identity" folder used to reside.
You can either select "Make alias" from the Finder's File menu, or command-option-drag the folder if you're familiar with that short cut. (Just Make sure it ends up named "Main identity" and not the "Main identity alias".
Eject the encrypted disk image. (Select it on Finder's Desktop and and pick "Eject" from the file menu or just type command-E.)
When you now launch Entourage, if you didn't place the password on the keychain when you created the image, you will be prompted for the password to the encrypted disk image
As long as the encrypted disk image is mounted (appears on your desktop), your mail is accessible. To protect it again, you will want to eject the encrypted disk image. Before you can do that, you'll need to quit Entourage and the Microsoft database daemon process. (Otherwise, Finder will tell you the image can't be ejected because it is in use.) To make it easier to do that, the following AppleScript can be used:
```
tell application "Microsoft Entourage" to quit
tell application "Microsoft Database Daemon" to quit
tell application "Finder" to eject "EncryptedMail"
```
You can download a copy of this script, "Eject Encrypted Mail", from my file sharing page.
Note that while the image is not mounted, you will also not get notifications of calendar appointments (since those are stored in the database.)
Remember that you will want to periodically backup the "EncryptedMail.dmg" file which contains your encrypted mail. If you back up the "EncryptedMail.dmg" file, then a password and an OS X system will still be needed to open the backup. Or you can open the encrypted image and back up its content without encryption.

If something above seems missing, confusing or down-right wrong, you can eMail me as car1son at my .Mac account. (Please be specific at what point things went wrong and how they went wrong.)

Good luck!