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Email Encryption

Our company is a small business company that has around 100 users with a Exchange 2010 environment and Office 2013 Clients. We are currently in discovery mode of understanding how to manage encryption of email to our clients. What is a good practice on deploying certificates to the end users and their clients? How do you handle password management with the certificates if the end users forget them? Is there any good plugins that work well with Outlook 2013? Is there any good mobile apps that work with email encryption for iPhone/Android? So far I have been testing with http://www.gpg4win.org and https://code.google.com/p/outlook-privacy-plugin/.
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Dave Howe
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