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Mail encryption research. Using exchange and multiple mail clients

We're considering encryption email.  We have Exchange 2010.  Our clients use Outlook 2010, 2013, Outlook for the Mac, Apple Mail.  

We also have mail on a mix of Apple and Android phones.  We have a large group of users that use Outlook Web Access.

Based on this information.  Are there any things we should be aware of before looking at different options?

I assume the best way is to manage this at a server level?
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This is a very broad questions.  But basically yes .. handle this at the server level.  Purchasing an SSL/Unified Communication cert will put you on the correct path.  This will enable using HTTPS for  OWA, it will allow you to force Encryption to handheld devices, enable you to force TLS with other servers etc.
If you are looking at encrypting all email from the clients that is sent out .. that is a whole other issue.  You would be looking at S/Mime and client certificates for signing/encryption.

 The barrier to encrypted email is not at the Exchange server. The problem is that the recipient has to be able to decrypt it.

So it works if you know who you want to send encrypted email to, and they are willing to set up to receive it. For a company that wants to communicate with another company, it can be great. But you can't just encrypt everything outside your organization and expect everyone to be able to read it.
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