Securing Outlook emails to clients

We have confidential docuemnts we need to send to our clients on a daily basis.  We are using Outlook 2007 clients which are connected to our Exchange Server 2007.  Our clients are using Outlook also usually connected to their ISP via a POP3 setup.  What is the best way to encrypt outgoing emails and attachments to them with a minimum of effort on their part as they have limited access to IT staff?
chasmx1Asked:
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MegaNuk3Connect With a Mentor Commented:
SMIME is a bit of a pain to implement...
As pmorton23 says, just use passworded zip files...
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pmorton23Commented:
you can password protect the attached document. you can setup tls on your last smtp server before the internet. basically purchase an SSL/TLS cert and install it on the smtp server. nothing needs to be done by the client for tls.
 
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MegaNuk3Commented:
Use PGP

Or the entrust eIntelligent server, but PGP is easier for small needs...
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pmorton23Commented:
pgp would require the client to install pgp and know a little something about it. all ISP's allow TLS encryption and requires nothing on the client end.
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MegaNuk3Commented:
Depends how secure you want the emails and attachments... Since the client is using POP, once the messages have been delivered to the ISP they will sit on the ISP mailboxes unencrypted...

Entrust eIntelligent message server will require no configuration on the email recipients end and will encrypt and sign the mails end-to-end.
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chasmx1Author Commented:
What about using a certificate between the two Outlook clients?
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pmorton23Commented:
then you should just setup pgp in that case. but you said client doesnt have IT and wanted minimal involvement. the easiest method would be to password protect any document with sensitive data. then give client password.
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chasmx1Author Commented:
Okay, thanks.
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