Microsoft email encryption

We are looking for a way to send encrypted email. There are times we need to send employees sensitive information and I want it to be safe. We all use outlook 2010/2013. Is the built in email encryption safe? Is it safe to use a free certificate provider (i.e. comodo)?
clifford_m71IT ManagerAsked:
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Alex GreenConnect With a Mentor 3rd Line Server SupportCommented:
To be honest it'd be easier zipping up the file and assigning a password to it.

However you can encrypt the message by using

http://office.microsoft.com/en-gb/outlook-help/encrypt-email-messages-HP010355559.aspx

If you want to assign a certificate to it you'll have to give all your employees private keys to decrypt the message.
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CubeOverCommented:
What is your definition of "safe"?
Encrypted emails are safer than unencrypted.
Free COMODO certs are better than no encryption.
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Rich RumbleConnect With a Mentor Security SamuraiCommented:
You have a few choices, S/MIME which is built-in to outlook or 3rd party software like PGP, GPG or even 3rd party solutions like Ironport where the email is stored encrypted, and you can send the access to a person via regular email. They login and look at the email via https and your invitation link. Or the easier and free route to use a good password on a zipped file. There are hundreds of ways to encrypt an attachment however there are very few universal ways to decyrpt it. Zip is standard on anything over XP, and S/MIME has been available since the 90's in outlook, but it's not as easy to use properly. http://en.wikipedia.org/wiki/S/MIME
With any encryption both sides have to have the tools to access the data, and it's often inconvenient to use 3rd parties that one has but the other doesn't.
I'd recommend using 7zip to create a ZIP archive that is encrypted and that uses the AES-256 library, see attached screenshot.
-rich
7zip.JPG
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clifford_m71IT ManagerAuthor Commented:
Thanks for the help. Using the built in Outlook encryption was too much effort. We are going to go with a third party, RPost. It allows up to 10 encrypted emails a month for free. That is more than sufficient for us.
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