I use Outlook and Office 365 through the Web and occasionally have to send messages that need to remain confidential and sometimes have to be revoked after a period of time. Is that possible in Outlook?
While Gmail might be the most popular Web-based email program there’s no denying that Microsoft’s done a great job with Outlook.com and its own Web based mailer. In fact, Outlook has a better interface and many more features and capabilities than Gmail, not to mention a vastly superior settings and preferences area that actually lets you know what you’re setting and how it will affect your experience.
Microsoft’s approach to encrypted email, however, might leave you a bit puzzled because it doesn’t use a password to keep the encrypted data secure. If your recipient can access their own email, they can decrypt and read the message. Then again, you can at any time remove external access so if you want to send a message and lock it down after a day or two, you can do that. Still, a shared password offers better security, though it’s hard to implement across email programs and once they receive the email, you no longer have control over it. Trade offs, for sure.
HOW TO ENCRYPT AN EMAIL MESSAGE IN OUTLOOK
To start out, let’s just write a suitably mysterious email message in Outlook:
Ahh, so mysterious about the secret rendezvous! To encrypt it before sending it to the recipient, click on the “Encrypt” button along the top. That will add the following to the message composition window:
Click on “Change permissions” and you can prevent things like email forwarding. But let’s just send it and see what happens…
The first thing to be aware of is that it is not encrypted in your Sent Mail folder:
On the other hand, that saved copy has the important link Remove external access. A click on that and you’ll be able to effectively revoke the recipient’s ability to read your email, even weeks later:
So that’s pretty cool. But what’s the experience like for the recipient?
READING ENCRYPTED OUTLOOK EMAIL IN GMAIL
Here’s what appears in the Gmail inbox:
Basically it’s a link to the message rather than the message itself. A click on “Read the message” and you’ll pop open a Web page that prompts for a secret key:
You can sign in with your Gmail credentials or you can request that a one-time secret code be sent to you, a two-factor authentication, except it goes to the same mailbox of the message itself.
Meanwhile, in another email message received in my Gmail inbox, I get this info:
The code is 98263316, as you can see, and it’s only good for 15 minutes. Of course, if I’ve already revoked read access from within Outlook it’s already unreadable even with the passcode sequence.
Once entered, however, I can finally read the email, albeit in its own Web browser window:
Notice that I can’t forward this email or respond to it here (though I could take a screen capture or photograph of the screen).
I think the greatest benefit of these encrypted email messages in Outlook is actually the ability to revoke access in the future. How many email messages have you sent where an hour, a day or a week later you wished you could cancel? If you get into the habit of using this encryption method for those volatile messages, you would have just that, though you won’t know if they read it prior or not.
But then again, maybe I’m looking at this wrong. Why do you want to use encrypted email and does the Outlook approach to message encryption meet your needs? Leave me a comment and let me know!
Pro Tip: I’ve been using and writing about Outlook and other Microsoft Tools since they were famous for BASIC. Yes, that long ago. Please check out my Outlook help area for more tutorials on this powerful program while you’re visiting. Thanks!
