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How To Send Secure Email For Free

06.26.09

Updated 22 JuL 2009 to correct and add links

Intro

These days a great amount of personal information is moved around the internet. Unfortunately most of it is done in clear text. That means it can be intercepted and read. Your financial or personal identification information can be compromised that way. Many businesses have provided ways to send secure, encrypted emails but most people can't do it from their personal computer using their personal email accounts. This is relatively easy to do and it's 100% free. It works in email programs like Microsoft Outlook, Outlook Express, Windows Live Mail, or other similar email programs. This does not work for email accounts that you access only by logging into a webpage. To be clear, in can be used for Hotmail, Gmail, or Yahoo mail if you use a client like the ones listed above to access that account.

I heard Steve Gibson of GRC.com describe how to get certificates for securing encrypted files and encrypted emails on his Security Now! podcast. Once you follow the steps below, you can use your new email certificate to send certified emails and encrypted emails that only the intended recipient can read. Remember, you must exchange emails "signed" with the certificates before you can send encrypted emails.

Steps:

1. Get and install the free certificate

I recommend you use Internet Explorer for this step. Go to Comodo's Free Secure Email Certificates . You'll need to provide your name,email address, your country, and a revocation password. Don't forget to remove the check mark from the box labeled "Opt in?" if you don't want Comodo's newsletter. Read the agreement and then click "Agree and Continue." You'll next see a page informing you that the Application is successful and details were emailed to your account.

Open your email program and open the new email from "Certificate Customer Services." The subject should read "Your certificate is ready for collection!" The details for getting the certificate and installing it are in that email. One option is to use a linked big red button. I could not use this option because my default browser is Firefox and that wasn't working for me. Instead, I copied the link ("Please visit https://secure.comodo.net/products/...") and pasted it into the IE8 address bar. Then I copied the "Collection Password" and pasted into the "Collection Password" box. Finally I entered the email address in that box. Click the button and allow any pop-ups necessary. You should see the page declare the install was "Successful."

The certificate will work indefinately. However the date on it does expire in one year. You can update it then. If you choose not to update it, it will continue to work but anyone receiving a signed or encrypted email from you will receive a warning that it is expired. That may cause them to question whether or not they can trust the certificate.

I recommended using IE because when I used Firefox 3.0.11 the process failed. If the process fails, send their support center an email from the account for which you applied for the certificate and ask them to revoke the certificate. In my case they took care of it very quickly.


2. Apply the certificate in your email program

To apply the certificate to your email account in your email program use Comodo's instructions at the following links:


For other email programs, try using your favorite search engine (Google, Yahoo, Bing) to find instructions.



3. Exchange signed emails

In order for you to exchange encrypted emails with friends, family, or businesses, you and the other person need to exchange signed emails first to provide eachother with the public part of the certificate. Signing an outgoing email will be slightly different in each email program. In Outlook 2007, you click the button near the top of the email window that looks like a yellow and red ribbon on a yellow envelope. In Windows Live Mail, you can right click an empty area in the toolbar of the email, select "Customize," then use the pop-up window to add the "Sign" and "Encrypt" buttons to the toolbar. Or you can look for "Digitally Sign" and "Encrypt" in the Tools menu of the menu bar. I prefer to have the buttons available rather than looking in the menu for it everytime.


4. Send encrypted emails

After you and the other person have exchanged emails digitally signed with secure certificates, you can send encrypted emails back and forth. When I used Outlook 2007, no further action was needed to send an encrypted email once the signed email was received. In Windows Live Mail, I had to create a contact with the other persons certificate to send an encrypted email. To do this:

  • a) Open the email from the other person that was signed with their digital signature certificate.
  • b) Click on the yellow and blue ribbon in the upper left corner.
  • c) This opens the "Signed" window. Click the "View Certificates" button near the bottom.
  • d) Click the "Add to Contacts" button.
After that sending encrypted emails was no problem.