How to Encrypt Emails in Outlook

A study of IT leaders across the US and UK revealed that 95% of leaders believe data is most at risk when using emails. Additionally, 83% of organizations have experienced email data breaches, out of which human error accounted for 24%.

Another report says that nearly two-thirds of organizations that fell victim to a data breach hadn’t encrypted their data. With email continuing to be the dominant form of business communication, the case for email encryption can’t be stronger!

Most businesses use Microsoft Outlook to share emails often containing sensitive information like personally identifiable information (PII), credit information, meeting agendas, budget documents, IT tickets, client information, etc. With so much confidential information being exchanged, it’s critical to secure emails in Outlook, considering rising cyber threats to businesses.

Furthermore, stringent data privacy regulations like HIPAA and GDPR, among others, regulate how PII should be treated. Incorrect handling of client data can cause companies to incur fines of up to €20 million!

As Microsoft Outlook continues to be one of the most widely used email clients, let’s explore how you can encrypt your emails in Outlook.

How to Send Encrypted Emails in Outlook

There are two primary encryption Office 365 Message Encryption options to secure and send encrypted emails in Outlook.

Option 1: Office 365 Message Encryption

You can use this option only if you have Office 365 email account or 365 subscriptions. (The encryption option is not available in Outlook 2013 and 2016 versions, or Microsoft Office one-time license purchases.) Plus, you can send an encrypted email to any email client – on Outlook servers or other email networks, such as Gmail.

Office 365 Message Encryption is a four-step process:

  1. Compose a new email like you normally do.
  2. Click on “Options” in the message bar and select “Encrypt” from the dropdown.
  3. Apply the relevant settings.
  4. Send encrypted message.

Your recipients will receive an HTML message, which they can download and open in a web browser or mobile app. However, there are no restrictions on attachments when it comes to protection – meaning, the recipient can choose to download them on their local machines, print, or forward them to others.

Option 2: Certificate-Based Encryption or S/MIME

This encryption technique is a bit complex than the Office 365 Message Encryption and involves exchange of public and private security keys to encrypt and decrypt emails. You need to purchase a security certificate from a certified provider and add it to your Outlook by following the guided instructions. Here’s how you can install the certificates:

  1. Click the File option in the top left of your Outlook window and select Options.
  2. Click Trust Center in the new window and choose “Email Security” from the settings.
  3. Click on Import/Export located under “Digital IDs”.

Once you finish all these steps, you can share the signed certificate with your recipient. Your recipients also must install the certificate and send you an email. When both of you exchange emails, you receive both public keys and private keys from each other that can be used to encrypt and decrypt emails.

How to Open Encrypted Emails in Outlook

Your email recipients will see a lock icon next to your email message, indicating the encryption. They will be asked to verify themselves. Once they do that, they can read the message like a normal email. However, there are a couple of limitations.

Limitations of Outlook Encryption Methods

Outlook offers simple methods to encrypt your emails but there are a few limitations:

  • The maximum message size you can send using Office 365 Message Encryption, including attachments, is 20 MB. This causes a serious inconvenience to businesses as they would either have to break file attachments to reduce the size to comply with the size limits (if the attachment size is over 20 MB), or look for easy file transfer options like cloud storage services. While the former method is time-consuming and practically infeasible, the latter option is fraught with security challenges.
  • There are some email usage restrictions with Office 365 Message Encryption mode, meaning unless you buy additional Microsoft add-ons - Information Rights Management (IRM) or Azure Information Protection (AIP), your recipient can easily forward, print, or download the attachments. This poses a serious risk to your confidential information, unless you are willing to shell out extra bucks, which again might not be a foolproof solution either.
  • When it comes to S/MIME, both sender and recipient need to install public certificates and buy them online from certified providers, making this process a bit expensive and hassling.
  • With S/MIME technique, if anyone gets hold of the private keys, then your data is at risk. Any tampering with public keys also messes up things. Plus, a recipient can read the email only on the device, which has the matching certificate. This makes the whole process really inconvenient for field professionals like sales.

There is a simple, yet effective way to get past these limitations by opting for an email solution that not only gives you superior encryption capabilities but also tops it up with additional features to make it even more user-friendly. RMail, an email security solution from RPost, is just what the doctor ordered!

RMail for Outlook

This is probably the easiest and the most powerful way to encrypt your emails in Outlook. Your recipients don’t need to install or set up anything on their device, sign up for an account, or purchase anything from any service provider.

And you can send encrypted messages to pretty much any email service like Hotmail or Gmail. All you need to do is install our RMail for Outlook app in Microsoft Outlook, restart your Outlook application, and start composing your email. As simple as that!

The encryption experience is as simple for your recipients as it is for you.

How RMail Helps You Easily and Securely Encrypt Emails in Outlook

RMail’s end-to-end encryption not just makes it easy to automate privacy and prove compliance with privacy regulations but also offers more. Each RMail message returns the highest level of court admissible, legally valid, timestamped email privacy compliance evidence in the form of a Registered Receipt™ authenticatable email record.

RMail uses dynamic double-layered encryption protocols to secure your emails smartly. And once you install the RMail add-in, you can see the “Send Registered RMail” button in your Outlook new message compose window. Let’s see how it works.

Encrypt Emails in Outlook
How to Send Encrypted Emails in Outlook

Transmission level encryption

Using RMail’s transmission level encryption feature to send a secure email is a simple process. All you have to do is compose an email, press RMail’s Send Registered button (you will get that after you install RMail), check the Encrypt box, and select the Transmission Level radio button. If the recipient’s system doesn’t support the TLS encryption, RMail Dynamic Encryption will automatically wrap the email content and attachments inside an AES 256-bit encrypted PDF. This way RMail guarantees 100% encryption, whereas with most email clients (e.g.: Outlook, Gmail), at least one in every 10 emails goes out unencrypted, with the sender not being able to know which.

Message level encryption

This is RMail’s password-protected, message level, end-to-end encryption option (AES 256-bit PDF encryption). The experience is just as great as with TLS; you simply press “Send Registered” and select the Message Level radio button. This Outlook encryption add-in also works with Office 365.

Encrypted Emails in Outlook
How to Open Encrypted Emails in Outlook

At this point, you can choose to create the password or leave empty for RMail to autogenerate one. Your recipients will get a password in their email along with the end-to-end encrypted message or attachment. RMail also offers a third option to allow your recipients to set their own decryption passwords. Your email will stand out in the recipient’s inbox thanks to the Registered Encryption markings in the subject line and the email body.

Beyond Encryption – Human Error Prevention and Personalized Training with RMail

RMail does more than just securing and sending encrypted emails while in transit or in the recipient’s inbox. Businesses are plagued by the growing Business Email Compromise (BEC) email impostors who use a familiar-looking domain name and email address of an authentic recipient to trick employees to accidentally send highly sensitive information.

RMail’s Human Error Prevention Kit has many email impostor detection AI technologies, such as RMail “Domain Age Detector” that will alert the sender right before they are about to reply to one of these newly created domain lures.

There is also this AI-infused data leak protection feature “RMail Recommends,” which solves the problem of users forgetting about fully utilizing their e-security technology. Set up to run inside the Microsoft Outlook, RMail Recommends uses advanced AI to detect in-the-moment-of-sending-email, whether or not the sender should be applying extra protections for that message and then applies them as needed. The AI engine learns from user behavior and adapts over time.

This brings several benefits for businesses:

- Raise cybersecurity awareness for your staff

- Deliver in-the-moment secure email recommendations

- Prevent important emails from going out unencrypted, which could be a bigger risk in terms of fines and reputation

Rmail Recommends Encrypt Emails in Outlook

Encrypt Your Emails with RMail

RMail for Outlook gives you 256-bit encryption to protect your sensitive emails and attachments. You just need to choose relevant settings. RMail offers various unique features within the encryption umbrella - email open tracking, proof of email delivery, electronic signature, large file transfer (up to 1GB in one go!), PDF conversion, metadata cleaning, and more.

Plus, RMail can be integrated with several other platforms – Gmail, Xerox, Salesforce, Zimbra, etc. RMail is easy, extremely secure, convenient, fast – and most important, much more affordable at scale. Try it to send secure emails for free!

You can get several encryption options in the market. Pick and choose what works best for you, but don’t leave your sensitive data and emails unencrypted – out in the cold. Because if you do that, chances are your business might not recover!