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Secure Email Outlook

by stacy

Three Ways to Encrypt Email in Outlook

Email providers such as Microsoft Outlook, which enjoys a long history of popularity in the professional sector, are adapting to address the growing security threats to their platform. They have developed robust encryption options to ensure that both the platform’s email and all its emails remain safe. The platform is compatible with three different methods of email encryption, including built-in and third-party add-ins. This allows users to have great control over how they send secure emails to Outlook, as well as receiving protected messages. There are many elements and information that one should consider when weighing the options for email encryption. It is important to know the identity of the recipient and the email address from which one wishes to send encrypted messages. The best encryption method for an individual depends on many factors, including ease-of-use, cost, features available, compatibility, and compatibility.

Method 1: Encrypt emails using certificates (S/Mime).

S/Mime encryption is a less current option to encrypt an email. It can only be used by users who use free webmail services like Yahoo and Gmail to send encrypted messages to users. S/Mime encryption is not widely supported. The service is available to anyone with an Outlook email account. However, everyone can’t use S/Mime. This method of encrypting an email can make it vulnerable to external attacks like message takeovers. It also increases the risk as users must exchange encryption keys to encrypt emails. Your emails will not be secure if the key is compromised.

Initial Setup to Encrypt Emails With S/MIME

Individuals should follow these steps to set up email encryption using S/Mime in Outlook

Obtain an email encryption certificate and import it into Outlook. Then, share it with the recipient(s). The sender should receive the certificate.

Many certificate authorities (CAs) can issue an email encryption certificate. Microsoft encourages individuals to use one of its preferred CAs, such as GlobalSign, Comodo, or IdenTrust if they wish to encrypt their email. It doesn’t matter what CA the user selects, it is important to make sure that the email security certificate, also known as S/Mime encryption or secure email certificate, is purchased. This is not the SSL certificate, which is more commonly advertised.

After the certificate has been purchased, the user will be sent both the certificate as well as the password to encrypt emails and import them into Outlook. The user must keep a copy of this certificate as well as its password. This certificate and password are required again if the computer or hard drive is damaged. It will be impossible to access encrypted emails that have been sent or received previously if they are lost. Recipients will have to complete the tedious task of replacing the old email encryption certificate with the new one if they need it.

After the certificate has been purchased and backed up, Outlook can import it by following the steps:

Click File (located in the top left of the Outlook window). Next, click Options. Then, click Trust Center (in the new window that appears). Next, click Trust Center Settings. In the left pane, click Email Security. Then, click Import/Export (located beneath the heading Digital IDs (Certificates). Alternatively, if the certificate has been installed onto the device by an organization’s IT staff, click Settings instead. Following the guidance of the IT staff, choose the correct certificate from those listed. Select the certificate file by clicking Browse. After that, click Browse to select the certificate file. Click OK to close the Trust Center window. The certificate has been successfully imported.

To share one’s certificates with intended recipients, a digitally signed message must first be sent to all recipients to whom one might — at one point — want to send encrypted messages. This task must be completed successfully

Begin composing a new message in Outlook. In the top menu bar of the new message window that appears, click Options. Then, click the small icon beside More Options. Click Security Settings… (located in the new Properties window that appears). Next, select Add digital signature to this message (located in the Security Properties window that appears). Alternatively, click Change Settings to access the specific certificate being used to digitally sign the message. The newly imported certificate should be used for this certificate. Click OK in this window. Next, click Close.

After completing the above steps, you will receive your public key that is associated with your certificate. This allows other people to encrypt the messages that are sent to the individual. One needs a private key to decrypt messages that have been received. This key is only accessible to the intended recipient/user and can be imported only within Outlook.

How to send encrypted emails in Outlook using S/Mime

The public key portion of the recipient’s certificate must be included to send encrypted messages. After recipients have received encryption certificates and sent digitally signed emails via Outlook or another S/Mime compatible platform, one can add their certificates to one’s contact information. To do so:

Open the digitally signed message sent by this specific recipient. Right-click the sender’s name and then click Add to Outlook Contacts (located where the From information corresponding to this message appears). If this recipient is already a contact, the Edit/Update option can be utilized rather than creating an entirely new contact. Next, click Certificates (located in the top ribbon of the contact card that appears). Then, select the proper certificate for this contact from the list of certificates that appear.

After this has been completed successfully, encrypted messages may be sent to the contact using these steps:

Start composing a message. Click Options in the top menu. Next, click the small icon beside More Options. Finally, click Security Settings in the Properties window. Select Encrypt attachments and message content in this window. Next, click OK. Next, close the previous window. Please note that subject lines are not encrypted. It is highly recommended that you do not include sensitive information in your subject lines. Just click Send. This email will be encrypted.

How your recipient opens your encrypted email

A recipient might need to open encrypted emails on their computer. They can also use Microsoft Outlook, which will automatically decrypt the message. This reply will be encrypted automatically if the recipient replies to this message.

Receive Secure Emails from Clients (Replies, New Emails).

Once the initial setup is complete, all recipients will be issued the required encryption certificates. This allows them to send encrypted replies seamlessly and with ease. You can also send encrypted emails by following these steps.

S/MIME Costs and Features to Encrypt Outlook Emails

After the initial setup is complete and certificates are properly shared, email encryption with S/Mime in Outlook can be used. It’s very user-friendly. We recommend that you only use this option for emails where the recipient has requested it. This is unlikely to happen if your company or professional practice serves large enterprises clients or government agencies. Small businesses and individuals will not be able to use S/Mime as they typically use free webmail accounts on platforms such as Yahoo and Gmail, and may not have the knowledge or resources to set this option up.

S/Mime can be used to encrypt emails. Users cannot access encrypted email outside of Outlook. Recipients may not be able to forward the encrypted email to others. S/Mime does not work with G-Suite GSSMO email accounts. These G-Suite email account must use IMAP instead.

S/Mime’s cost varies widely. The certificate prices for Microsoft’s recommended CAs ranged between $39 and $369 annually in 2019. If multiple years have been paid in advance, this recurring fee must be renewed every year or every 2-3 years. This is also the cost of one certificate per user. Each user within an organization is charged a separate fee.

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