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Internal and External Encryption

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Hi,

I'm currently struggling at some probably basic encryption question. I hope someone can give me a hint...

 

I've got a customer migrating from Notes to Exchange 2013.

They are running a PGP gateway which takes care of external encryption.

In Notes they used to user-enforce encryption (PGP or S/MIME) by a button or adding "#" in the beginning of the subject field. As the Notes guy told me, they are manipulating the Mail header so the original un-encrypted mail is delivered to the encryption gateway for external encryption if the mail is addressed to internal and external recipients. Internally it is encrypted by Notes itself.

My question is, how can I achieve something similar with exchange and such a gateway? Is there a way to encrypt mails internally by utilizing an internal Server 2008 PKI and externally by the encryption gateway (while addressing the mail to internal and external recipients at the same time)?

 

Thanks!



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