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How to Send Encrypted Email in Outlook: Step-by-Step Tips

How to Send Encrypted Email in Outlook: Step-by-Step Tips

Tutorial
- August 15, 2024
-3:46 AM
-
- by Pro VPN Advice

As a Microsoft 365 subscriber, I’ve found sending encrypted emails in Outlook is now easier. The Encrypt button makes it simple to keep my messages safe¹.

The Encrypt button in Outlook gives me options like S/MIME and IRM (Information Rights Management). But, the S/MIME option only shows up if I’ve set up an S/MIME certificate on my computer¹.

To use S/MIME encryption in Outlook, I first need to set up a certificate on my computer’s keychain¹. Then, I can turn it on in Outlook¹.

Microsoft 365 subscribers can also use Microsoft 365 Message Encryption to send secure emails¹. This feature comes with the Office 365 Enterprise E3 license, so more users can use it¹.

The Encrypt-Only feature is for Microsoft 365 Apps for enterprise users who use Exchange Online¹. Also, Outlook 2019 and 2016 users have different steps to encrypt messages, like choosing Permissions instead of the Encrypt button¹.

Email Encryption in Outlook Made Easy

Benefits of Encrypting Emails in Outlook

Encrypting emails in Outlook keeps sensitive info safe and communication secure. It stops unauthorized access, preventing data breaches. This ensures your messages stay confidential².

Prerequisites for Outlook Email Encryption

To encrypt emails, you need a valid S/MIME certificate on your computer. This method needs both sender and receiver to have the right certificates¹.

Microsoft 365 users can use the Microsoft 365 Message Encryption (OME) feature. This cloud option offers extra encryption types, like Encrypt-Only and Do Not Forward, without managing certificates¹.

Encryption Method	Description
Certificate-based encryption	Requires installation of public certificates by both parties²
Office 365 Message Encryption (OME)	Built-in feature for encrypted emails using Outlook or other email clients²
Third-party extensions	Available for encrypting messages in Outlook without purchasing Office 365²

Using these encryption options, Outlook users can make their email safer. They can protect sensitive info from breaches².

Configuring S/MIME Certificates for Encryption

Before you start using S/MIME encryption in Outlook, you need to set up your S/MIME certificates. This means adding the certificate to your device’s keychain and setting it up in the Outlook Trust Center. Once done, you can use S/MIME encryption to protect your emails.

Setting up S/MIME Certificates in Outlook

Setting up S/MIME certificates for Outlook is simple. First, get a valid S/MIME certificate from a Certificate Authority (CA) or use a free option like Actalis, an Italian CA³. Then, add it to your device’s keychain and set it up in the Outlook Trust Center.

Outlook makes it easy by automatically importing the S/MIME public key from signed emails. This lets you send encrypted messages to contacts right away³. You can also change the security level to High if you need more protection³.

For those who need to send encrypted emails, like with FormSmarts, you’ll need to submit a Certificate Addition Request and sign a message in Outlook³. You’ll get a confirmation email quickly after adding the S/MIME certificate to the service³.

Keep in mind, S/MIME encryption only works with messages to and from people in your organization’s address list. Also, digital signatures work best with recipients in your organization⁴. If no one in your organization has a certificate, you can’t send encrypted messages⁴.

For a smooth setup, make sure you have a valid Personal Information Exchange (PFX) certificate on your device. Also, make sure S/MIME is turned on for your Exchange accounts⁵. With these things ready, you can set up your S/MIME options in the Outlook app. Choose certificates for signing and encryption, and decide if you want to automatically sign or encrypt your messages⁵.

By following these steps, you’ll be ready to use S/MIME certificates and protect your Outlook emails⁴³⁵.

⁴³⁵

Encrypt Emails Using S/MIME in Outlook

Encrypting emails with S/MIME in Outlook is easy and keeps your messages safe. Here’s a simple guide:

Compose a new email message in Outlook.
Click on the Options tab in the email composition window.
Locate the Encrypt option and select it.
If you have an S/MIME certificate, Outlook will encrypt the email and attachments before sending.

More people are using S/MIME to send secure emails in Outlook⁶. Many companies give out S/MIME certificates for safe email⁶. Also, more Outlook users are installing the S/MIME control for secure emails⁶. When you get an encrypted message, you’re often asked to install the S/MIME control.

For Microsoft 365 users, it’s key to know if S/MIME works on Chrome in Active Directory domains⁶. It’s also important to see how often S/MIME controls are installed across different browsers⁶. How many users trust their domain to use S/MIME for encrypting emails shows how well this feature is used.

Using Outlook’s S/MIME encryption keeps your important emails safe from prying eyes. This makes your online chats more secure.

Encrypt with Microsoft 365 Message Encryption

If you’re a Microsoft 365 subscriber, you can use the built-in Microsoft 365 Message Encryption feature. This feature helps secure your emails. You can choose to encrypt your emails with “Encrypt-Only” or “Do Not Forward” options. This keeps your emails and attachments safe even after they reach the recipient’s inbox⁷.

Encryption Options for Microsoft 365 Users

Microsoft 365 offers three main encryption options: Microsoft Purview Message Encryption, Secure/Multipurpose Internet Mail Extensions (S/MIME), and Information Rights Management (IRM)⁷. If your organization isn’t an E5 customer, you can try Microsoft Purview solutions for 90 days⁷. You can apply encryption in two ways: by the service or as a customer control⁷.

S/MIME is a top choice because it needs public keys for each recipient for secure messages⁷. It’s recommended to use OME for sending sensitive info to outsiders, IRM for setting usage rules, and S/MIME for messages between peers⁷. But, using more than one encryption method on a message might cause problems, so pick the best one for your needs⁷.

Microsoft 365 also protects email data at rest with BitLocker Drive Encryption⁷. You can use third-party tools like PGP with Microsoft 365, but be aware of PGP’s limits in the platform⁷.

Encryption turns emails into cipher text for privacy⁸. Admins can set rules to automatically encrypt messages, and sensitivity labels help keep emails in line with company rules⁸. You can also make encrypted messages look more like your brand⁸.

Only certain Office 365 plans let you use Office 365 Message Encryption (OME) services⁹. S/MIME works in Outlook on the web, Outlook 2010, and later, but only if you have the right Office 365 plan⁹. People outside your organization can’t open messages protected with S/MIME⁹.

In Outlook 2016 and 2019, you can encrypt messages one by one or all at once by setting it up⁹. Admins can also set up mail flow rules in the Exchange Admin Center to encrypt messages automatically or remove encryption added by users⁹.

how to send encrypted email outlook

Keeping your private info safe is key in today’s digital world. Outlook’s email encryption tools offer a solid way to do this. If you often send out sensitive stuff or just want to keep your chats private, learning to send encrypted emails in Outlook is a big plus¹.

Sending Encrypted Messages Step-by-Step

To send an encrypted email in Outlook, just follow these easy steps:

Start by writing a new email as you usually do.
Then, go to the “Options” tab in the email window.
Find the “Encrypt” button and pick either “S/MIME Encryption” or “Microsoft 365 Message Encryption” based on your Outlook setup¹.
If you choose S/MIME Encryption, make sure your S/MIME certificates are ready in Outlook¹.
For Microsoft 365 Message Encryption, you need an Office 365 Enterprise E3 license or higher¹.
After picking your encryption method, your email will be sent securely, keeping its contents and files safe¹.

You can also set up rules to automatically encrypt emails that fit certain conditions, like who it’s sent to or what it says. Just go to the “Options” tab, then “Rules and Alerts,” and set up the encryption settings¹.

By doing this, you can easily add encrypted email to your Outlook routine. This way, your important info stays safe¹.

Reading Encrypted Emails in Outlook

As an Outlook user, I can easily read and reply to encrypted messages. This is true whether I have a Microsoft 365 subscription or not. For Microsoft 365 subscribers, accessing encrypted emails in Outlook is easy. I can view and reply to them just like any other message¹⁰.

Users with other email accounts might need to do a bit more to get to the encrypted content. Depending on the sender’s email provider, I might need a temporary passcode or to sign in to a web portal¹⁰. This makes sure only the intended person can see the confidential info, adding an extra security layer.

Outlook makes reading encrypted emails easy, no matter my email account type. The encrypted messages are right in my Outlook inbox, so I can handle them like any other email¹⁰. This makes it easy for me to stay on top of my emails and keep my info safe.

Using Outlook’s encryption, I know my sensitive info is safe. And I can still easily check my emails through a familiar interface¹⁰. This mix of security and ease makes Outlook great for handling encrypted emails in both work and personal life.

Encrypting All Outgoing Messages by Default

As an Outlook user, you can easily make your email send encrypted messages by default. This setting in the Trust Center makes sure every email you send is secure. It keeps your messages private and safe¹¹.

To do this, go to the Trust Center in Outlook’s settings, then click on the Email Security tab. Check the box to “Encrypt contents and attachments for outgoing messages.” With this on, Outlook will automatically encrypt every email you send. This keeps your important info safe from others¹².

Open Outlook and go to the File menu.
Click on Options, then select Trust Center.
In the Trust Center settings, select the “Email Security” tab.
Find the “Encrypt contents and attachments for outgoing messages” option and check the box to enable it.
Click “OK” to save the changes and close the Trust Center.

By doing this, all your future emails will be encrypted by default. You won’t have to worry about sending messages without encryption. Outlook will take care of it for you¹¹¹².

Encryption Method	Advantages	Disadvantages
S/MIME Encryption	Widely supported encryption standard Provides end-to-end encryption Allows digital signing of messages	Requires both sender and recipient to have digital certificates installed Can be complex to set up and manage
Office 365 Message Encryption (OME)	Easier to set up and use compared to S/MIME No need for digital certificates Supports encryption for emails sent to external recipients	Requires an Office 365 subscription with the necessary features May not offer the same level of granular control as S/MIME

Using Outlook’s encryption, your important messages stay safe, even if you forget to encrypt them. This default encryption is a simple way to make your emails more secure¹¹¹³¹².

Encrypted Email Forwarding and Attachments

When you send encrypted emails in Outlook, the encryption stays when you forward them to others¹⁴. But, how attachments work can change based on your encryption choice.

Attachment Encryption Behavior

Choosing “Encrypt-Only” keeps Microsoft Office files like Word, Excel, or PowerPoint safe after the recipient downloads them¹⁴. But, files like PDFs or images can be downloaded without encryption¹⁵.

With “Do Not Forward”, all attachments stay encrypted, even if the recipient downloads them¹⁴. This adds an extra security layer for your important files.

Remember, the encryption options and how they affect attachments depend on the recipient’s email service and client¹⁶. For example, Outlook.com users with a Microsoft 365 subscription can open encrypted attachments in their browser. But, others might need to sign in with an email provider ID or a one-time passcode¹⁶.

Knowing how encrypted email forwarding and attachments work in Outlook helps keep your sensitive info safe when sharing it with others¹⁴¹⁶¹⁵.

Outlook Encryption vs Traditional TLS

Microsoft Outlook offers different email encryption options compared to traditional Transport Layer Security (TLS). TLS encrypts the connection between the email client and the recipient’s server. But, the message might not stay encrypted once it reaches the server¹⁷. Outlook’s encryption, like S/MIME and Microsoft 365 Message Encryption (OME), keeps the message and attachments encrypted after they arrive¹⁷.

Outlook uses TLS to encrypt emails by default¹⁷. OME adds another encryption layer for Microsoft 365 users¹⁷. To use OME, you need a premium Microsoft 365 subscription, like Microsoft 365 Family or Personal¹⁷. But, there are concerns about the security of OME due to some research findings¹⁷.

For S/MIME encryption, you need an eligible Outlook app or a premium subscription¹⁷. S/MIME encrypts emails with user-specific keys, which requires some technical setup and verification¹⁷. Most end-to-end encryption plug-ins for Outlook are for businesses¹⁷.

Services like Proton Mail offer easy end-to-end encryption, password-protected emails, and more¹⁷. Proton Mail also has a tool to move and encrypt emails, contacts, and calendars from Outlook¹⁷.

In summary, Outlook’s encryption options offer more security than traditional TLS, but they have their limits and concerns. Knowing the differences between Outlook encryption and TLS helps users make better choices about their email security¹⁷¹⁸.

Feature	Outlook Encryption	Traditional TLS
Encryption Level	Message-level encryption with S/MIME and OME	Connection-level encryption during transport
Encryption Type	User-specific keys (S/MIME) or Microsoft-managed keys (OME)	Shared session keys
Encryption Scope	Message content and attachments remain encrypted	Message may not remain encrypted at recipient’s server
Setup Complexity	Requires technical setup and verification for S/MIME	Typically easier to implement and configure
Availability	S/MIME in Outlook desktop, OME in Microsoft 365 premium plans	Widely adopted across email service providers

Recipient Experience with Encrypted Emails

When you send an encrypted email from Outlook, how easy it is for the recipient to open it depends on their email setup¹⁹. If they use Microsoft 365, they can easily read and reply to these emails in Outlook, on the web, or on their mobile. But, if they use other email services, they might need to do more, like use a temporary code or sign into a web portal, to see the encrypted message and files.

Reading Encrypted Emails Outside Outlook

For those not using Outlook or Microsoft 365, getting into encrypted emails can take a few more steps¹⁹. Some encryption tools like Zix and ShareFile make it easy for recipients, but they might cost more based on what the user needs¹⁹. Mimecast also has an email encryption option, but we don’t have exact numbers¹⁹. A video shows how to turn an email into a password-protected PDF. This PDF can be opened on any device, including Outlook, mobiles, and web-based email.

This PDF encryption uses AES256 encryption, which is very secure¹⁹. Even though older Acrobat had some issues, the latest encryption is now strong and safe¹⁹.

The way people experience encrypted emails can differ, but with the right tools and setup, anyone can open and read these emails, even without Outlook or Microsoft 365²⁰. Keeping strong encryption, like using the right certificates, setting up two-factor authentication, and keeping software updated, makes email communication safe and smooth for everyone.

Troubleshooting Encrypted Email Issues

Sending and receiving encrypted emails in Outlook can sometimes be tough. Users might find it hard to open encrypted messages, send them, or even see the Encrypt button²¹.

These issues can come from many places. For example, it could be because of Microsoft 365 subscription limits, wrong tenant setup, or not having the right licenses for Microsoft Purview Message Encryption²¹. To fix these, check if your organization has the right subscription, make sure the tenant is set up right, and ensure everyone has the needed licenses²¹.

Users should also check their Azure Rights Management service connection and make sure sensitivity labels are correct²¹. Sometimes, signing out of Office, clearing cached credentials, removing unlicensed accounts, and reconnecting to Azure Rights Management with PowerShell can solve the problem²¹.

Organizations having trouble with sending or getting encrypted emails outside should look at their Conditional Access policies and guest account settings²¹. Users within the same group can open encrypted emails from shared mailboxes using certain Outlook versions or Outlook on the web, even if they came from another place²¹.

Other ways to fix encrypted email issues in Outlook include fixing wrong hostnames²², making sure the device’s clock is right²², turning off any broken add-ins²², and checking if SSL ports are open²². Also, checking the security certificate name and changing the SMTP server port can help²².

If nothing works, fixing corrupted Outlook email files with a tool like Repairit for Email might be needed²².

Conclusion

Outlook’s email encryption features, like S/MIME and Microsoft 365 Message Encryption, are great for keeping emails safe²³. Users can set up certificates and pick the right encryption to protect their emails. This way, they keep their messages private and secure.

With more cyber threats and laws like HIPAA and GDPR²³²⁴, encrypting emails is a must for many industries. Tools like Digify’s Outlook encryption add-in offer a secure choice over Outlook’s basic encryption. They help users keep their private data safe and avoid fines for not protecting sensitive info.

In short, using Outlook’s encryption tools lets you send encrypted email in Outlook safely. It’s important for professionals in finance, law, or healthcare, or anyone who wants to keep their emails private. These encryption methods give you peace of mind and security in our digital world.