I have used Gpg4Win in the past along with FireGPG to have encryption on my emails. I am needing to roll this out to quite a few more people and was wondering if anyone else had some products they preferred better. The criteria I need is free and as user friendly as possible. I looked at MailCloak but I have had some issues with it on 1 of the 2 computers I've been testing on. It seems like it might work pretty well as a overall solution but on my computer I keep getting "Identity cannot be created." and not sure whats going on with that. Thanks for the info.
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Just to end this subject since it didn't have any hits. I ended up going Gpg4win on all of the Windows machines that were in question. It is very easy to install and has built in support for various email clients, mainly Outlook. Mailcloak still gave me issues, so in the end I used FireGPG as a Firefox add-on and it integrates perfectly into Gmail. If you are using other types of Webmail programs you simply have to click on Tools --> FireGPG --> Encrypt and to get the same encrypted email outcome.