Encryption/Password options

Client have started discussing the possible need that for some of their emails that they send to their clients the should be sending them either/or password protected or encrypted.  Does Outlook or Adobe have an option for this or would they need to purchase special software?

  If additional software is needed, what do you recommend.
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Tiras25Asked:
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ks_adminConnect With a Mentor Commented:
There is an option (add-in) that you can set up a secure point to point SSL session between two exchange servers..  much like a VPN from one company to another.  Very cumbersome, and not entirely useful unless you email a specific business(es) frequently.

We went with a third party option from Sophos, and it's an appliance.  Our specific appliance is also our SPAM filter, but I don't think you have to buy both..  I could be wrong.  Try this link:

http://www.sophos.com/en-us/products/email/email-security-and-data-protection.aspx

ks_admin
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Sean MeyerConnect With a Mentor Commented:
Here is the way to do it in outlook --
http://office.microsoft.com/en-us/outlook-help/encrypt-messages-HP006369952.aspx

Then there are the companies willing to do it for you --  Zix is one of the biggest.  (Pricey)
http://www.zixencryption.com/ZixCorp-Bundles.asp

Or the following --   $7 / month
http://www.senditsecure.com/home.aspx
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Tiras25Author Commented:
So by doing it in Outlook...  is it free?  Does that mean the recepient should have the same time encrytion enabled to decrypt?  

Please advice..
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gtkfreakConnect With a Mentor Commented:
If you want to encrypt e-mail messages during transmission, you have to use SSL email certificates or PGP / GnuPG. The difference between SSL and PGP certificates is that for SSL, you need to purchase a certificate from Verisign, or any other Certifying Authority. With GnuPG, you can create a certificate to encrypt your emails yourself. However, with GnuPG or PGP, the recipient too must have PGP or GnuPG. You should go with SSL Certificates, as it is easy for both yourself, and the recipient to get one.

Refer these links for more information:
http://www.gpg4win.org/
http://www.gpg4win.org/doc/en/gpg4win-compendium.html
http://www.verisign.com/authentication/digital-id/?tid=gnps

You can easily install SSL email certificates into Microsoft Outlook. However, for PGP/GnuPG, you will mostly need to use the Thunderbird email client.

Before paying up for a Verisign certificate, you can try out Comodo SSL free email certificates and then go for Verisign. Comodo provides free SSL certificates at this URL, http://www.instantssl.com/ssl-certificate-products/free-email-certificate.html. There are many more providers for these certificates, besides Verisign or Comodo.
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Tiras25Author Commented:
Thanks for the advice.

I guess I really need to ask the client what exactly they need it for and how they expect to use it.  If they use it with other firms so they need to have the same certificate for the handshake.  Or of they email vendors for example, they don't need to use it.  Knowing this client is very tight, they would go for something very cheap.

What would you guys recommend?
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