How To Send Encrypted Email In Gmail, Outlook, Android & iOS

This tutorial explains the step-by-step process to send an Encrypted Email in Outlook, Gmail, iOS, and Android devices with screenshots. You will also learn to open Encrypted Emails:

Encrypting email is the process of encoding and decoding your messages so that they can remain safe and secure from intrusive third-parties. These third-parties could be hackers, business rivals, or unfriendly governments.

Email encryption can be a complex subject but the way that it is sent and received is relatively simple. There are several options available and they can vary in price and complexity. In this tutorial, we will learn the basics of email encryption and will also see how we can apply it in a practical way.

How to Encrypt Email_

Encrypted Emails

Email-encryption

Knowing that someone could hack your emails is disturbing. If you make the effort to encrypt your emails, then you’ll lessen the chances of this happening. While nothing can be made 100% secure, it is better to make the effort to defend your privacy.

A data breach could pose a serious risk to your privacy or to your business. You have a legal and ethical obligation to protect them as much as you reasonably can. No one will want to do business with you if you have a history of being repeatedly hacked.

Types Of Email Encryption

#1) S/MIME (Secure/Multipurpose Internet Mail Extensions): S/MIME is based on non-Sequential cryptography and allows the sender to sign the message to enable verification.

#2) PGP/MIME (Pretty Good Privacy): PGP/MIME sends the message as a whole and also includes the attachments. It is the main alternative encryption protocol.

#3) SSL/TLS (Secure Sockets Layer/Transport Layer Security): SSL/TLS is the standard protocol in relation to moving emails from the sender to the receiver. It is a basic requirement of sending emails.

#4) Third-Party Encryption Services: This is a software that you can download and can be used within minutes of being purchased. Be aware that the quality varies, hence research is required.

#5) STARTTLS: This is an email command protocol which instructs an email server that an email client wants to turn an insecure connection into a secure connection.

How To Open An Encrypted Email

Open an encrypted email

[image source]       

Encrypted email is useless if you don’t know how to open it. The following set of instructions apply to Gmail but the other email providers follow a fairly similar method. Make sure to conduct your own research if you have a different email provider in order to avoid confusion.

  1. Open the email in the usual manner by pressing on it with a left-click.
  2. Click on the download arrow.
  3. Now click on the ‘’Save’’ button at the bottom of your screen.
  4. Then proceed to click on the ‘’Open’’ button. This will open up ‘’Encrypted Message’’.
  5. Click on a message called ‘’Use a One-Time Passcode’’.
  6. You’ll see a message stating that a once-only code has been sent to your Inbox.
  7. Once you’ve opened up your Inbox, copy and paste the code that has been sent to you.
  8. There is a box on the ‘’Encrypted Message’’ page where you write in the code.
  9. After you’ve written the code, click on ‘’Continue’’.
  10. You should be able to read the encrypted message after a few moments.

How To Encrypt Emails

This applies when you’re sending an email. Of course, different email services have their own methods of doing this. When using a mobile phone or tablet ensure to take note of how an iOS and Android platform is capable of having its emails encrypted.

#1) How To Send Encrypted Email In Gmail

Gmail is capable of sending an encrypted email because it has S/MIME embedded within it. However, it is necessary for both the sender as well as the recipient to activate it if it is to be operable. This is only available with G Suite.

You can enable S/MIME by taking the following steps.

Here is a brief summary of how to enable S/MIME for Gmail. Be aware that it can be much more complicated than this.

  1. Make sure to sign in to your Google Admin account.
  2. Take the following pathway. Apps -> G Suite -> Gmail -> User Settings.
  3. In Organization, select the domain name you want to be enabled.
  4. Go to the S/MIME setting and select the box that is listed as Enable S/MIME encryption for sending and receiving emails.

When it shows time to compose the message, just write your email as you normally would and then click on the lock icon which is next to the recipient on the right.

In order to change the level of encryption click on ‘’View Details’’. This can enable you to view the encryption levels that are present.

Green (S/MIME enhanced encryption) encryption : It is currently protected by S/MIME protocol and it will need a private key to be decrypted.

Gray (TLS – standard encryption) standard encryption : It is protected by TLS. Both the sender and receiver need to be compliant with TLS if the message is to be sent successfully.

Red (no encryption) No encryption icon: It means that no encryption protocol is operational.

#2) How To Encrypt Email In Outlook

You’ll need a Digital ID to encrypt emails with Outlook. It is compliant with S/MIME but only after a digital ID or certificate has been obtained from the administrator. Take the steps mentioned below in order to encrypt Outlook.

 encrypt Outlook

[image source

Here is a brief summary of that process.

#1) Obtain a certificate and add it to the keychain.

#2) Go to Files. Options -> Trust Center -> Trust Center -> Trust Center Settings.

#3) On the left side, choose Email Security.

#4) Under Encrypted Email, go to Settings.

Trust Center - Outlook

#5) There will appear an option called Certificates and Algorithms.

#6) Click Choose and select the S/MIME certificate. Press OK.

Certificates and Algorithm

Once it is installed you can take the following steps to send an encrypted email.

  1. Go to the Gear Menu and click S/MIME settings.
  2. You can either encrypt the entire message and the attachments or you can add a digital signature to all the emails.
  3. Click on the three dots box and it will allow you to encrypt the message. Be aware that the recipient needs S/MIME enabled otherwise the message will not be readable.

#3) How To Encrypt Emails On iOS

S/MIME is the default encryption method for iOS. This page gives a full explanation.

#1) In Advanced Settings there is a S/MIME switch. Turn it on.

iphone6-ios8-settings-encrypt_by_default 1

#2) Turn on the yes option for the ‘’Encrypt by Default’’ toggle setting.

#3) Make sure to press the lock icon while composing a message. This will be next to the recipient.

composing a message 1

#4) The blue lock icon blue lock icon means everything is OK.

#5) The red lock icon Red Lock means the recipient needs to turn on their S/MIME setting.

#4) How To Encrypt Emails On Android

Android is capable of hosting both S/MIME and PGP/MIME. CipherMail will help you to encrypt emails by using Gmail as its default setting along with some other apps.

Ciphermail

[image source

The other option is to use PGP. For this, you’ll need a keychain to place your certificates and an email provider that is compliant with PGP protocol.

#5) How To Encrypt Emails Using Other Services

Some of the email encryption services provide a push-button service such as Protonmail that requires you to simply click on a button just before you send a message.

ProtonMail - Email encryption

Other services such as Mailbox require you to select the Options menu, click on More Options, and then click the dialogue box launcher. When you’ve reached this point you can click on Security Settings, and only then you can finally select Encrypt.

So obviously some services are a lot more complicated than others. Perform a simple Google search and you’ll learn whether the email encryption service you’re thinking about is the right one or not.

Examples Of Email Encryption Services

  1. Symantec Gateway
  2. Trend Micro
  3. ProtonMail
  4. SecureMail
  5. Posteo
  6. SCRYPTmail
  7. Tutanota
  8. Proofpoint Email
  9. Kolab Now
  10. Mailbox
  11. Egress
  12. Mailfence
  13. PreVeil
  14. Virtru
  15. Workspace ONE
  16. Hushmail.
  17. Countermail
  18. Runbox
  19. Startmail
  20. Ciphermail
  21. Zoho Mail
  22. Egress
  23. Trend Micro
  24. Send 2.0
  25. Enlocked

Frequently Asked Questions

Q #1) How safe are encrypted emails?

Answer: The only way to be 100% sure that you won’t be hacked is to send your data by snail mail. There may be times when this is still necessary.

Email encryption makes your messages relatively ‘’safer’’ than if you hadn’t encrypted them. The key thing to do is to take ‘’reasonable’’ measures that are expected from you.

Q #2) What else can I do to keep my emails safe?

Answer: There are a number of other things that you can do to make sure that your emails are safe.

These are enlisted below:

  • Make sure your computer is free from malware or bugs.
  • Purchasing a VPN service will help to make hacking your computer harder.
  • Choose a strong password.
  • Make sure that the questions that are required to be answered while opening from a new computer can only be answered by you.
  • Two-factor authentication should be seriously considered as another layer of security.

Q #3) Are there any Compliance issues?

Answer: Yes. Be aware that S/MIME works with Gmail, Outlook, and iOS devices. PGP/MIME works with Yahoo, AOL, and Android devices. Always read before trying to obtain an encrypted email service.

Q #4) Which method is the best?

Answer: A combination of all the factors that have been listed would be optimal if you’re to encrypt and secure your emails. However, by using S/MIME you are using a method that is popular and widely understood.

While PGP can protect messages, it can also be more challenging to use correctly. However, good communication is the key.

Q #5) Which email encryption service is the best?

Answer: From a practical viewpoint, Gmail would be the best as it is the most widely used email provider in the world and it is much more widely understood. This indeed would make it relatively simple to operate.

If you use one of the most obscure email encryption services then some training is required to avoid confusion and frustration. Good training is crucial. If you do want to go for the best possible encryption service then Send 2.0 is recommended as it promises military-grade performance.

Q #6) I’ve never had my emails hacked. Why should I care?

Answer: This is simply not a professional attitude to have. If it does happen then how will it reflect on you? Chances are you’ll end up very sorry.

Q #7) Which email providers require third-party support?

Answer: Yahoo, AOL, and Android will all need this extra step to enable email encryption. Yahoo and Android are both S/MIME and PGP/MIME compliant while AOL will work with PGP/MIME only.

Some Points To Remember

  • SSL encryption is indicated by ‘’https’’ at the start of a web address rather than ‘’http’’.
  • A public key will encrypt an email.
  • A private key will decrypt an email
  • Both PGP/MIME and S/MIME require the sender and the recipient to install security certificates.
  • PGP doesn’t require a digital signature in advance to send an encrypted email.
  • When a message is sent it is protected by a Public Key Infrastructure (PKI).
  • PKI employs both private and public keys.
  • Email encryption is required to protect both Data at Rest as well as Data in Transit.
  • Data in Transit is an email that is being sent.
  • Data in Transit is the information that is being saved on the cloud, files or documents.
  • STARTTLS can only work if a valid certificate is present in the receiver’s email server.
  • A lot of email services require third-party downloads in order to solve compliance issues.

Conclusion

Encrypting emails is a sound business practice, especially while handling sensitive information. There is no excuse for doing this when there are so many great options available to do this. The only way to find the best solution is through research.

By knowing how to safely send and receive encrypted emails, we can provide a safe environment for business communications to occur. This is the minimum standard that is expected from clients and third parties.

Happy Reading!!