How to Send a Secure Email

If you’re like most people, you probably check your inbox at least 1-3 times per day, according to Statista

That’s 1-3 opportunities to receive malware or other malicious threats straight to your inbox, as 94% of malware gets delivered via email according to Verizon’s 2019 Data Breach Investigations Report.

And, with the average cost of a data breach being nearly $4 billion in 2019 and smaller organizations (up to 250 employees) being the most likely target for a malicious email (1 in 323 per email security company Symantec), it’s clear that the way people normally approach email is not very safe.

So what is to be done about it? Stop using email at all or not open or send any attachments?

That’s not the solution.

That’s burying your head in the sand.

The solution is to learn how to send secure email attachment.

And that’s what I’m going to teach you to do in this article.

It’s Time to Start Encrypting Your Emails

Encrypting your email, including messages and attachments you send out to someone will save you a lot of trouble.

Unfortunately, most email providers don’t even bother with encryption (at least not by default) and let their users fend for themselves against malicious attackers.

This can be a big problem, especially if you need to send some personal or financial information. 

Scammers are becoming more and more sophisticated and cunning in their phishing attacks.

You need to know how to identify and avoid these fraudulent attempts.

For instance, with Discover it Secured, the emails you receive will always have your full name (as displayed on your credit card) in the greeting line. 

So, instead of “Hello customer!”, it will read “Hi John Smith”.

Another sign that there’s something “phishy” will be the “urgency” that the email will portray, whether that means sending your Social Security number, ID, credit card number or something else.

Discover it Secured will never ask you to send this information directly via email.

That said, if you’re using Gmail or Outlook, all is not lost and you can still send secure email attachment. 

It just takes a little tinkering with it.

How to Encrypt Outlook Messages

With Outlook, you have two encryption options for sending secure documents via email:

To encrypt messages on Outlook with S/MIME, you’ll first need to set a signing certificate on your computer. 

Once you have that, you can configure the certificate for your Outlook account as well.

Here’s how it goes:

  1. Go to the File menu and follow this path: Options>Trust Center>Trust Center Settings.
  2. Next, click on Email Security in the left pane.
  3. Find Certificates and Algorithms and select an S/MIME Certificate. Click OK.

You can also encrypt a single message.

To do this:

  1. Click on File and select Properties in the email message you want to encrypt.
  2. Go to Security Settings.
  3. Check the box Encrypt Message Contents and Attachments.
  4. Compose your email and click Send.

Now on to Gmail.

How to Send a Secure Email in Gmail

Gmail is by far the most popular email provider in the world.

Unfortunately, it’s also the most susceptible to malicious threats, phishing, malware, scams and so on.

That’s not to say that Gmail completely lacks in privacy and security, but these take second or third place to ease of delivery and use. 

Now, by default, Gmail uses TLS (Transport Layer Security). This is the successor of SSL (Secure Sockets Layer, so they can often be used interchangeably (although TLS is the newer version).

G Suite users, however, can also enable S/MIME for extra protection.

To do this, both the sender and the recipient must have S/MIME enabled and they also must exchange security “keys” with each other.

With that out of the way, here’s how sending secure document via email works:

  1. Compose your message and add your recipient in the “To” field.
  2. Depending on the recipient’s encryption level, there will be a lock icon on his right. Click on that lock.
  3. By selecting View Details you can learn more about the recipient’s encryption level or modify your S/MIME settings. S/MIME encryption levels are (from lowest to highest): Red, Gray and Green. Never send any personal information to someone with a red S/MIME level.

If enabling S/MIME seems like too much of a work, another option to send a secure and anonymous email via Gmail is to use a 3rd-party extension like SecureGmail.

You can install it from the Chrome Web Store.

Once you have it activated on your Gmail, you should see a lock icon next to your Compose button.

You’ll need to click on that lock if you want to write an encrypted email. 

Two things will happen:

  1. The header will now display Secured along with the lock symbol below New Message and,
  2. The Send button will now become Send Encrypted.

Once you hit Send Encrypted, you’ll need to enter a password in the pop-up window,

The recipient will need this password to decrypt your email. However, as this will only give them a hint about the password, you’ll need to send it to them in a separate message.

Encrypt Your Email, but without Extra Configuration and Installing Plugins

Let’s be honest. Just to configure encryption, whether S/MIME or PGP on Gmail or Outlook takes extra effort.

Even if you do everything right on your end, the other side also needs to do the same on their end. 

And even then, you can’t be 100% sure that you are sending secure document via email.

As I said previously, encryption is not at the top of the priority list for a commercial email service like Gmail.

Which is why, if you want to send a secure and anonymous email, you should use an encrypted email service like CTemplar.

With CTemplar you get a much better email security through 4096-bit encryption. This will do much better job of keeping your inbox safe from malicious threats. 

Not only that, but CTemplar also won’t keep any logs of your usage or track your IP, making it truly and 100% anonymous.

On top of all that, you don’t have to worry about 14 Eyes as your emails will be stored on secure servers in Iceland, which has some of the best privacy laws in the world.

So, if you want to send and receive secure email messages and attachments, start using CTemplar now.