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Many Exchange Server administrators balk at implementing Microsoft Outlook email encryption, because it has to be supported by both the sending and receiving email clients.
In other words, if I encrypt an email and send it to you, you can generally only decrypt the email by using the same software I have. If that software is proprietary or difficult to work with, the headache of encrypting email can outweigh its benefits.
A number of common free/open-source packages lessen the burden of email encryption -- but again, users have to go through the trouble of integrating them with their email packages to use them.
A creative workaround for this problem is an email encryption program for Microsoft Outlook 2003 called MessageLock. MessageLock works by compiling an email and its attachments into a standard .ZIP file that is secured with AES 256-bit encryption.
Since the vast majority of .ZIP utilities can decipher AES-encrypted .ZIP files (including WinZip, PKZip, TugZip and WinRAR), recipients probably already have the software they need to unpack and read the MessageLock-encrypted email messages.
MessageLock integrates into Microsoft Outlook and lets you access its functions through a button bar. Attachments can be separately encrypted as well.
The product can be installed on up to three computers at a time and works with any variety of email account (Exchange Server mailbox, POP3, etc.). It automatically decrypts any inbound messages encrypted with MessageLock, and can use AES-256, AES-128, Zip 2.0 or ML-256 encryption.
Users can also configure exceptions -- for instance, not to encrypt certain types of files or to only encrypt messages to specified contacts. If a recipient is also using MessageLock, the process is even more seamless. But anyone with a .ZIP utility should be able to make use of MessageLock-encoded messages.
A free and fully functional 30-day trial version is available from the manufacturer. Purchase price is $39.99. The only caveat is that the passwords used to open email need to be negotiated separately with the target users, of course.
About the author: Serdar Yegulalp is editor of the Windows Power Users Newsletter.
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WinZip offers a package called WinZip Companion that does the same thing, but I believe it is more reasonably priced for what you get.
—James S.
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Thanks for bringing WinZip Companion to my attention; it looks really interesting. I'll look into it for a possible future tip.
—Serdar Yegulalp, tip author
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Could you please explain why this workaround is effective if any user able to open a zip file can open the encrypted file?
—Abel B.
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They can open the zip file, yes, but they will not be able to open it unencrypted without the proper password. I mentioned in the article that the password for opening any given message needs to be negotiated between sender and recipient beforehand.
Obviously this isn't a complete solution for encrypted email, but it's one way to handle the problem.
—Serdar Yegulalp, tip author
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I saw the thread about WinZip Companion. I just wanted to point out that MessageLock has a lot more features and flexibility than WinZip Companion.
Encryptomatic has posted a comparison at its site: "How does MessageLock compare with WinZip Companion?"
—Cory A.
Do you have comments on this tip? Let us know.
Related information from SearchExchange.com:
Learning Center: The Microsoft Outlook Toolbox
Expert Advice: Time lag opening and sending encrypted email
Expert Advice: Best encryption method for an Outlook .PST file
Reference Center: Exchange Server message encryption resources
Reference Center: Outlook and Exchange Server administration tools
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