Please qualify your question with more details. Encrypted e-mail is too general a topic for me to help as it is.

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I don't know what direction to address. Is your question about an individual working with a mail client at home on their Mac and using Outlook? Is your question for an organization or company that has an industry or compliance need to use mail that is encrypted? Is your questoin about protecting mail that is sent over the Internet from prying eyes? Are you reacting to the hype around a flaw in PGP, that really is a flaw in mail clients and not encryption?

It's a business that exchanges documents with sensitive customer info. This includes medical data, social security numbers, invoices and billing, addresses, etc. They need to be able to encrypt the body of the email message along with any attachments that go with it, and have the recipient be able to receive them without installing software on their computer. Virtru seems to be exactly what they need, but the problem is that it's not available for Mac. I'm thinking I'm going to install parallels + win10, then I can install the virtru plugin for Outlook. After that, they only need to click a button to make the next email they send encrypted, and the recipient receives a message with a link to click to read the message.

The only problem with this plan is teaching the idiots how to get their documents into windows to attach them in outlook. It's a clumsy solution, and I'm looking for a better one.

Anything that requires managing keys or software is out of the question. I have to be able to do the work for them, show them what button to push, and walk away. Jaladattanagra wrote: Just spoke to rackspace on the phone directly. The tech support person there had no idea what I was talking about. He put me on hold several times to ask his colleagues, but after 30 minutes, responded with 'we don't offer that service.' Leslie, where would I find instructions to set up transport rules?

Is this a configuration that needs to be done on the email server, and if so, how do I access these settings considering I'm not in control of those servers? You would need an Enterprise 365 license to encrypt in 365. Other options are to route your mail through a hosted filter that allows you to encrypt via the subject.

Something like Barracuda could work. Just put #encrypt in the subject and poof, it's encrypted. Barracuda is one I am familiar with, but there is also GreenView and a slew of other hosted email encryption services. Edited May 16, 2018 at 13:23 UTC.

Davidr4 wrote: jaladattanagra wrote: Just spoke to rackspace on the phone directly. The tech support person there had no idea what I was talking about. He put me on hold several times to ask his colleagues, but after 30 minutes, responded with 'we don't offer that service.' Leslie, where would I find instructions to set up transport rules? Is this a configuration that needs to be done on the email server, and if so, how do I access these settings considering I'm not in control of those servers? You would need an Enterprise 365 license to encrypt in 365.

Other options are to route your mail through a hosted filter that allows you to encrypt via the subject. Something like Barracuda could work.

Just put #encrypt in the subject and poof, it's encrypted. Barracuda is one I am familiar with, but there is also GreenView and a slew of other hosted email encryption services. +1 for the Barracuda solution. It really is almost as easy as #encrypt and your done.

It still requires training the users to tag the emails. Appreciate the Barracuda Networks mentions! We offer Email Encryption as a part of which provides key email encryption policies such as Recipient-Based, Sender-Based, and Domain-Based to provide greater email protection from ever changing threats. It fully integrates with a cloud-based email encryption service for outbound email. Email that matches policy or is marked for encryption via the Barracuda Outlook Add-in is sent securely via TLS to the Barracuda Message Center, using AES with 256-bit keys to encrypt email.