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/.
ITimagingAsked:
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Dave HoweSoftware and Hardware EngineerCommented:
Ok, from the top then.

1) s/mime is the default for email encryption - largely because it is built into most email clients, outlook not being an exception there. PGP is less well supported, and in many cases you are better served looking at a gateway device (such as pgp universal gateway) where you can do the key management yourself rather than leaving it to your users.

2) key management is not hard if you centrally issue the keys, and keep a copy. If you want users to create and manage their keys, then commercial pgp has a "corporate key" function that allows you to insist all mails are encrypted both to your user's key and a corporate recovery key.

3) the cheapest way to get started with X509 (s/mime) in an exchange environment is just to issue the keys centrally yourself. there is an automated process for this using a system microsoft call "autoenrollment" (see the MS website for details) or you can just use something like XCA

4) what gpg, s/mime and most other solutions have in common is that you must have the key of the recipient already before you can send them any mail. gpg use a system of keyservers to allow you to "pull" a key from the internet, plus you can send them out of band for manual import. s/mime have a system where the key is sent with digitally signed mail, so the easiest way to get a key is to have your correspondent send you such a digitally signed mail, accept the key, then use it to send encrypted mail.
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Encryption

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