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How to Send Encrypted Emails: Secure Your Messages Now

Julia McCoy
Thursday, 2nd May 2024
how to send encrypted email

The thought of unwanted eyes scanning your personal messages gives you pause before hitting ‘send’. Maybe it’s a confidential business deal, a personal secret, or just something you don’t want the whole world to know. Whatever it is, you need to keep it safe.

That’s where email encryption comes in. It’s like a virtual envelope that seals your message shut, so only the intended recipient can open it. No more worrying about hackers, snoops, or accidental forwards.

But do you know how to send encrypted emails? It might sound too techie but it’s easier than you think.

In this post, we’ll break down step by step how to send encrypted emails so you can start sending secure messages like a pro.

Table Of Contents:

How Does Email Encryption Work?

Email encryption is a process that protects the content of your email messages from being read by anyone other than the intended recipients. It works by using cryptographic algorithms to scramble the contents of an email, making it unreadable to anyone who intercepts it during transmission.

The benefits of encrypting emails are clear: in terms of email security, it helps protect sensitive information, maintain privacy, and comply with data protection regulations like HIPAA, GDPR, and PCI DSS.

By encrypting your emails, you can safeguard personal data, financial details, or confidential business communications from being accessed by hackers, cybercriminals, or other unauthorized parties. It’s a crucial step in maintaining trust and confidentiality in both personal and professional communications.

Types of Email Encryption

There are two main types of email encryption: end-to-end encryption and transport layer encryption.

End-to-End Encryption (E2EE)

  • Purpose: E2EE ensures that data is encrypted from the point of origin to the point of destination and can only be decrypted by the intended recipient.
  • Usage: It’s commonly used in messaging apps, email services, and file-sharing platforms where privacy and confidentiality are critical.
  • Implementation: E2EE typically involves encrypting data on the sender’s device, transmitting it securely over a network, and decrypting it only on the recipient’s device, meaning the service provider or any intermediaries cannot access the plaintext data.

Transport Layer Security (TLS)

  • Purpose: TLS provides secure communication over a computer network, typically between a client (like a web browser) and a server (like a website).
  • Usage: It’s commonly used for securing web browsing, email transmission, instant messaging, and other types of data transfer over the internet.
  • Implementation: TLS encrypts data during transit between the client and the server, ensuring that it cannot be intercepted or tampered with by unauthorized parties. It operates at the transport layer (Layer 4) of the OSI model.

Key Differences

  • E2EE encrypts data from end to end, meaning only the sender and recipient can access the plaintext. In contrast, TLS encrypts data during transmission over the network but may not provide end-to-end encryption if data is decrypted at intermediate points (e.g., by a server).
  • E2EE is typically used for direct communication between users, while TLS is used for securing communication between clients and servers on the internet.
  • E2EE is often implemented in applications and services, while TLS is implemented in networking protocols like HTTPS, SMTPS, etc.

Some popular email encryption protocols include Secure Sockets Layer (SSL), Secure/Multipurpose Internet Mail Extensions (S/MIME), and Pretty Good Privacy (PGP). Each has its own strengths and weaknesses, so it’s important to choose the right one for your needs.

how to send encrypted email

Image Source: Norton

How to Send Encrypted Emails

Now that we understand the importance of email encryption, let’s dive into how to actually encrypt emails.

Step 1: Choose an Email Provider With Encryption

The first step in sending encrypted emails is choosing an email provider with encryption features. Some popular options include ProtonMail, Tutanota, and Hushmail. These providers offer varying degrees of encryption and may have different setup processes, so it’s important to research and choose the one that best suits your needs.

When selecting a provider, consider factors like the level of encryption provided, ease of use, compatibility with other email services, and any additional security features they offer.

Step 2: Enable Encryption in Your Email Settings

Once you’ve chosen an encryption-enabled email provider, the next step is to enable encryption in your email account settings. This process will vary depending on the provider you’re using.

For example, with ProtonMail, encryption is enabled by default for all messages sent between ProtonMail users. However, for messages sent to non-ProtonMail addresses, you’ll need to set a password or use the recipient’s public key to encrypt the message.

Be sure to follow your email provider’s specific instructions for enabling and configuring encryption settings.

Step 3: Compose an Encrypted Email

When composing an encrypted email, you’ll typically need to select an encryption option before sending the message. This may involve choosing an encrypt button or toggling an encryption switch.

Some providers may require you to select a specific recipient from your contact list who has a public key available, while others may have you set a password for the recipient to use when decrypting the message.

It’s important to double-check that encryption is enabled before sending any sensitive information.

Step 4: Send an Encrypted Email

Once you’ve composed your encrypted email and ensured that the appropriate encryption options are selected, you can send the message just like you would a regular email.

However, depending on the recipient’s email provider and settings, they may need to take additional steps to decrypt and read the message. This could involve logging into a secure web portal, using a specific email client that supports the encryption method used, or entering a password you’ve provided.

To avoid any confusion or issues, it’s a good idea to communicate with the recipient beforehand and provide clear instructions on how to decrypt and access the encrypted email.

What is Public Key Encryption?

Public key encryption, also known as asymmetric encryption, is a method commonly used to secure email communications. It involves the use of two keys: a public key and a private key.

While the concept may sound complex, understanding how it works can help you better protect your sensitive information when sending emails.

How Public Key Encryption Works

In public key encryption, the public key is freely available and can be shared with anyone who wants to send you an encrypted message. When someone uses your public key to encrypt an email, the message can only be decrypted using your corresponding private key, which you keep secret.

This ensures that even if the encrypted message is intercepted during transmission, it remains unreadable to anyone who doesn’t possess the private key. The recipient uses their private key to decrypt the message and read its contents.

how to send encrypted email

Diagram from SSL

Generating Public and Private Keys

To use public key encryption for email, you first need to generate a public and private key pair. The process for this varies depending on the mail app or encryption software you’re using.

In some cases, your email provider may generate the keys for you automatically when you enable encryption in your account settings. In others, you may need to use a separate encryption tool like GnuPG (GPG) or OpenPGP to generate your keys.

When generating your keys, you’ll typically be asked to provide a name and email address to associate with the keys, as well as a secure passphrase to protect your private key. Be sure to store your private key securely and never share it with anyone.

Sharing Your Public Key

Once you have your public and private key pair, you’ll need to share your public key with anyone who wants to send you encrypted emails. There are several ways to do this, such as uploading your public key to a key server, publishing it on your website or social media profiles, or sending it directly to your contacts via email.

Some email providers, like ProtonMail, automatically share your public key with other users of the same service, making it easier to send encrypted messages within the platform.

When sharing your public key, it’s crucial to ensure that you’re distributing the correct key and that it hasn’t been tampered with or replaced by a malicious actor. Some key servers and encryption tools provide key verification methods to help ensure the authenticity of public keys.

Popular Email Encryption Methods and Protocols

When it comes to securing your email communications, there are several popular message encryption methods and protocols to choose from.

Let’s take a closer look at three of the most common options: S/MIME, PGP/MIME, and TLS.

S/MIME Encryption

S/MIME (Secure/Multipurpose Internet Mail Extensions) is an email encryption protocol that uses digital certificates to secure email communications. It provides both encryption and digital signing of emails, ensuring the confidentiality and integrity of the message.

To use S/MIME, both the sender and recipient must have an S/MIME certificate issued by a trusted certificate authority. The sender’s email client uses the recipient’s public key, contained within their certificate, to encrypt the message. The recipient’s email client then uses their private key to decrypt the message.

S/MIME is widely supported by popular email clients like Outlook, Apple Mail, and Thunderbird, making it a convenient choice for many users.

TLS for Email

Transport Layer Security (TLS) is a cryptographic protocol that provides encryption for email during transmission between email servers. When an email is sent using TLS, the connection between the sender’s and recipient’s email servers is encrypted, preventing unauthorized access or tampering during transit.

However, it’s important to note that TLS does not encrypt the actual content of the email on the sender’s or recipient’s devices. While TLS protects the email from being intercepted during transmission, it does not provide end-to-end encryption.

TLS is widely supported by email providers and is often used in conjunction with other encryption methods, like S/MIME or PGP/MIME, to provide a more comprehensive security solution.

PGP Encryption

Pretty Good Privacy (PGP) is an encryption method that uses public key cryptography to secure email communications. Developed in 1991, it has been widely adopted by privacy advocates and security-conscious users.

PGP uses a combination of symmetric and asymmetric encryption to protect the confidentiality and integrity of email messages. The sender encrypts the message using the recipient’s public key, and the recipient decrypts the message using their corresponding private key.

While PGP is highly secure, it can be more complex to set up and use compared to other encryption methods, as it often requires the use of separate encryption software and key management practices. However, for those who prioritize security and privacy, PGP remains a trusted and reliable option.

Best Practices for Sending Encrypted Emails

Encrypting your emails is a great first step in protecting your sensitive information, but to truly ensure the security and effectiveness of your communications, it’s important to follow best practices.

Here are some key tips to keep in mind when sending encrypted emails.

Protect Sensitive Information in Emails

One of the primary reasons to use email encryption is to protect sensitive information from unauthorized access. When sending emails containing personal data, financial details, legal documents, or confidential business information, always encrypt the message to ensure that only the intended recipient can read its contents.

Be mindful of the types of information you include in your emails and consider whether encryption is necessary for each message. In some cases, it may be more appropriate to use a secure file-sharing service or encrypted messaging platform for particularly sensitive data.

Use a Custom Email Domain

Using a custom email domain, like yourname@yourcompany.com, can provide several benefits for your encrypted email communications.

First, it enhances your professional image and credibility by demonstrating that you’re serious about your business and online presence.

Second, a custom email domain can provide an additional layer of security by allowing you to implement organization-wide encryption policies and manage user permissions more effectively.

With a custom domain, you have greater control over the security settings and can ensure that all employees are using the same encryption methods and best practices.

Update Encryption Keys Regularly

To maintain the security of your encrypted email communications, it’s crucial to regularly update your encryption keys and software. Over time, encryption algorithms can become outdated or vulnerable to new attacks, making it necessary to upgrade to stronger and more secure methods.

Most email providers and encryption software will prompt you to update your keys periodically, but it’s a good idea to set reminders for yourself to check for updates at least once every few months.

When updating your keys, be sure to securely distribute your new public key to your contacts and verify that they are using the most up-to-date version when sending you encrypted messages.

Also Read: How to Send Large Files Over Email

Troubleshooting Common Issues with Encrypted Emails

While email encryption provides a valuable layer of security for your communications, it’s not uncommon to encounter issues when sending or receiving encrypted messages. Let’s take a look at some of the most common problems and how to troubleshoot them.

Recipient Unable to Decrypt Messages

One of the most frequent issues with encrypted emails is when the recipient is unable to decrypt the message. This can happen for several reasons, such as using the wrong public key, the recipient not having the necessary software or browser extensions installed, or the message being corrupted during transmission.

To troubleshoot this issue, first verify that you have used the correct public key for the recipient. If you’re unsure, double-check with the recipient or consult their public key directory.

Next, ensure that the recipient has the appropriate software or browser extensions installed to handle the encryption method you used. For example, if you use PGP/MIME encryption, the recipient will need a compatible email client or a browser extension like Mailvelope to decrypt the message.

Incompatibility With Email Clients and Extensions

Compatibility issues between different email clients and extensions can sometimes cause problems when sending or receiving encrypted emails. For example, if you use S/MIME encryption but the recipient’s email client doesn’t support it, they may be unable to decrypt the message.

To avoid these issues, communicate with your recipients beforehand to ensure that you are using compatible encryption methods and that they have the necessary software or extensions installed.

When possible, use widely supported encryption protocols like S/MIME or PGP/MIME to minimize the risk of compatibility problems.

Problems With S/MIME Certificates

If you encounter problems with your S/MIME certificates, such as error messages or inability to encrypt messages, you may need to check that your certificates are properly installed and up-to-date.

First, ensure that you have a valid S/MIME certificate installed on your device. If your certificate has expired or been revoked, you’ll need to obtain a new one from a trusted certificate authority.

Next, check that your email client is properly configured to use your S/MIME certificate. This process may vary depending on the email client you’re using, so consult your client’s documentation or support resources for specific instructions.

If the problem persists, try removing and reinstalling your S/MIME certificate, or contact your email provider or IT support for further assistance.

Also Read: How to Unsend Emails

FAQs: How to Send Encrypted Email

How to send an email with encryption?

Pick a secure email service, turn on encryption in settings, then compose and shoot off your message.

How do I encrypt an email on Gmail?

In Gmail, click the lock icon next to the recipient field. Choose “S/MIME” if it’s available for extra security.

How can I encrypt an email for free?

Use services like ProtonMail or Tutanota. They offer end-to-end encryption without costing you a dime.

How to send documents securely via email?

Encrypt the document before sending or use encrypted email services that protect attachments too. Double down on privacy.

Conclusion

Sending encrypted emails is a smart way to protect your sensitive information and keep your communications private. Whether you’re using a built-in encryption feature, a third-party tool, or a secure email service, you’ve got options.

Remember, the key is to make sure both you and your recipient are on the same page. Agree on an encryption method, exchange public keys if necessary, and double-check that your message is encrypted before hitting send.

By knowing how to send encrypted emails, you’re always in control of your communication privacy and won’t ever have to worry about who might be reading your messages.

Written by Julia McCoy

See more from Julia McCoy
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