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Email Encryption Microsoft Office 2007 Add-on

Posted on 2013-02-04
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Last Modified: 2013-02-06
Hi everyone,

I have been researching for the last two weeks for an Outlook Plugin for email encryption. I was initially looking into PGP software but I can not seem to find the right one. Ideally we were looking for software that would give our users a public key and private key.

Enigmail has all the features I am looking for but it would need to be for Outlook and not Thunderbird. Spending a little bit of money would not be an issue either.

So the Prereqs would be

- A plugin
- Not extremely expensive
- For about 5 users on the same mail domain

Thank you in advance

Matt
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Question by:meshoxford
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by:rscottvan
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Outlook has this functionality built-in.  You can read about it here:
http://office.microsoft.com/en-us/outlook-help/encrypt-e-mail-messages-HP001230536.aspx
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by:Dave Howe
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There are three major families of encryption that interoperate with email - the first is pgp as you have noticed, and the thunderbird plugin is called enigmail. For outlook 2007, you can use http://www.cumps.be/nl/blog/read/gpg-in-outlook-2007-outlookgnupg but the setup is rather manual. (note, both this and enigmail use gnupg, a compatible open source program)

If you are happy to pay, the original pgp program has gone though many corporate masters and is now back with symantec. the "desktop" encryption product gives you 2003/2007/2010 office support (for a price) - they also have programs for mobile platforms so you can access your encrypted mail "on the go"

The second (referenced by rscottvan) is s/mime, and is the same technology you are familiar with from certificate protected (https) sites. Exchange/Outlook is heavily integrated with this, with the ability to centrally issue keypairs from exchange/active directory, and even standalone outlook can use s/mime (called "digital IDs" by microsoft)

Note, both of these have a near-fatal flaw. you must, before sending to anyone, obtain *their* public key, and actually persuading correspondents to do this is pretty difficult.

The third class of scheme has a large number of (non-interoperable) providers and is called "oracle based encryption" (not related to oracle the corporation). With OBE, you communicate with a central server who will give you the encryption key for the recipient *even if they don't have one* and new users are invited to visit the central server, sign up for a (free) account, and decrypt their mail using that mechanism. Subscribers of course see this as transparent - a gateway product encrypts or decrypts the mail while in transit, so that they just use outlook as normal.

Some providers are Microsoft ( EHEE ) ZixCorp ( ZixMail PGP ( GEE ) and last but certainly not least, Cisco ( CRES )

The third solution can be scarily expensive though (Zix is cheapest, cisco probably most costly), so find out how much before you sign up :)
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by:meshoxford
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Thank you both for the replies.

@rsscottfan - We do not have an exchange server. Sorry I should of wrote that in my summary. We use a linux mail server exim from hosting.com. I am playing around with outlook at the moment.

@DaveHowe

Thank you for that well thought out response. I looked into Zix and that seems to be about 100 dollars a user a year... I am currently reading the cumps link that you sent me. Have you ever used it before? I think that I will give it a try. Let me know what you would personally recommend.

Thank you,

Matt
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Dave Howe earned 500 total points
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cumps? no, I use thunderbird with enigmail, as we use outlook 2010 here and it isn't compatible with the newer solution. If you aren't an exchange site though (or more accurately, pop3) then you could use this also:

http://sites.inka.de/tesla/gpgrelay.html

which is a single-host intercepting proxy that allows you to send and receive gpg encrypted mail with any pop3+smtp mail client.
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by:meshoxford
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Thank you for explaining everything
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by:Dave Howe
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You are welcome. I am just happy to see someone moving to use pgp - its an awesome system, and the core of some other solutions (such as hushmail and the debian maintainer system)

Best of luck :)
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