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How to Send a Secure Email to Someone: Step-by-Step Guide

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

That’s 1 to 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.

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

So what is to be done about it? Stop using email, or do not open or send any attachments.

That’s not the solution.

That’s burying your head in the sand.

The solution lies in embracing end-to-end email encryption.

It’s Time for Email Encryption

Email encryption is the process of disguising the contents of an email, including the body, subject line, and any attachments, so that only the intended recipients can read them using a decryption key.

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 offer more than the most basic level of encryption (at least not by default) and let their users fend for themselves against malicious attackers.

This can be a big problem, especially when sending sensitive 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 “fishy” 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.

If you’re using Gmail or Outlook, all is not lost, and you can still send secure email attachments. 

We will show you how to send secure email with both Outlook and Gmail.

How to Send Encrypted Email in Outlook

With Outlook, you have two email encryption options for sending sensitive information:

  • Office 365 Message Encryption (with the Azure Information Protection add-on)
  • S/MIME Encryption

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 also configure the certificate for your Outlook account.

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 how to send secure email in Gmail.

How to Send an Encrypted Email in Gmail

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

Unfortunately, Gmail’s level of encryption isn’t very high.

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

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 (Secure Multipurpose Internet Mail) for extra protection.

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

With that out of the way, here’s how to send secure email attachments in Gmail:

  1. Compose your message and add your intended recipient in the “To” field.
  2. Depending on the recipient’s level of email encryption, there will be a lock icon on his right. Click on that lock.
  3. Selecting View Details lets you 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 potentially sensitive information to an email account with a red S/MIME level.

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

You can install it from the Chrome Web Store.

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

You’ll need to click on that lock 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 must send it to them in a separate message.

Encrypt Your Email but without Extra Configuration and Installing Plugins

LLet’sbe honest. Configuring email 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 must do the same on their end. 

And even then, you can’t be 100% sure you are emailing secure documents.

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

What is the most secure way to send email?

You should use an accurate end-to-end encrypted email service like Mailtrain to send a secure email.

With CT Mailtrain, you get much better email security through 4096-bit encryption. This will do a much better job of keeping your inbox safe from malicious threats and data breaches.

Additionally, Mailtrain won’t keep your usage logs or track your IP, making it honestly 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 Mailtrain now.

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