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What is the best way to encrypt emails sent from a server running Windows 2008 R2?

I need to be able to send encrypted emails from our server running Windows 2008 R2 to remote users.

Remote Users will be using a RemoteApp via RDP gateway to connect to one of our servers and will create and save  txt files on the server that will need to be emailed to them. Some of these txt files will contain sensitive data and will need to be encrypted.  What is the best way to accomplish this?
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n2fc
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Best way to encrypt email is via Public Key Encryption Certificates.

See: http://www.comodo.com/home/email-security/free-email-certificate.php

Comodo offers free secure email certificates that are easily installed into most email client programs (like Outlook, Netscape, etc.)  
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Member_2_1239314

If you need to prove the identity of the sender, you will need to get an SSL Certificate verified by either Comodo, Thawte, Equifax or Verisign. There are multiple providers and you can choose your pick.

You can also use GnuPG or PGP to do the same task, if you just need to encrypt email and do not need to legally prove identities when sending email. See http://www.gnupg.org, http://www.pgp.com for more information.
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Dave Howe
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DaveHowe:

Thanks for your in depth response to my question.

Didn't think of route #3. Since we already have a Sharepoint Site that would greatly simplify
the process.   Thanks for saving me a lot of time by bringing solution #3 to my attention.
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ASKER

Great answer. Thank you.