Finding out if email addresses support secure transfer of messages
The problem
There are thousands of email providers out there that offer free email services or come bundled with web hosting accounts, DSL services or dialup internet. Security, however, is often not the primary concern for these providers. Since many of the services are provided for free, cost needs to be kept as low as possible. Encryption costs money because it requires more CPU cycles per message, meaning that a server can process fewer messages - so you need more servers.
Many users are now security conscious enough to realize that reading email on an unencrypted connection is not the best idea, especially when using public WLAN hotspots and the like. So most email providers secure webmail interfaces with HTTPS and many even offer encrypted transfer of email via the IMAP, POP3 and SMTP protocols. What many users fail to realize though is that even though their mail is transmitted between their computer and the email service via a secure connection, it may well be transmitted to other email servers completely unprotected. That's because many providers still haven't enabled encryption for server to server transmissions.
While this is probably not a major issue for users in most democratic countries, it can become a problem in less liberal societies where internet connections are closely monitored and writing the wrong thing in an email could easily get you into trouble (or your company's trade secrets exposed, if that's what you are more worries about).
What to do
It's important that users are aware of the problem and have an easy way to check what happens to their email once it leaves their own computer. Checking for encryption on the back end of email servers is not all that complicated to a tech minded person, but to make it easier for the average user, I've created a little web tool that combines all the necessary tasks into a simple web form and gives them a clear yes/no answer when they check for the encryption capabilities the server for a certain email address supports (or doesn't).
By going to the IsMyMailSecure website, everyone can check if an email address supports encryption. Just enter the email address in the form, press the submit button and wait a few seconds. If the system already knows the servers for the address, the answer will come instantly. If it's a new domain, the checks will take a moment, but the system will remember the results for a while afterwards. Note that if you want to be sure you are communicating securely with someone, you need to test both your own email address and that of the other person. And if you're worried what will happen to your email address when you enter it on the site, feel free to just use a randon name before the @ sign - it gets stripped off anyway before any of the tests are run.
If you notice that IsMyMailSecure shows the servers for an address to be not secure, you may want to consider switching to a different email provider. Encryption between servers is not the ultimate security measure that will make all your worries go away, but it's an important element in the overall security concept. You may want to avoid providers that don't provide the bare minimum of security to their users.
Questions and Answers
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