Send and Receive Encrypted Email Messages

Summary

Explains how to send an encrypted email message by adding [encrypt] to the subject line, how a recipient opens and reads an encrypted message, and how to resolve the error caused by an outdated Outlook encryption add-in. Applies to Bowdoin students, faculty, and staff and to outside recipients of encrypted Bowdoin email.

Body

Questions

  • How do I send an encrypted email message?
  • How do I make sure only the intended recipient can read a message?
  • How do I read an encrypted email message that was sent to me?
  • I received a notification that an encrypted message was sent to me. How do I open it?
  • How does someone outside Bowdoin open an encrypted message with a one-time passcode?
  • Why did I get an error when I tried to send an encrypted message?
  • The old Outlook encrypt button no longer works. What should I do?

Environment

This article applies to Bowdoin students, faculty, and staff who send encrypted email from a Bowdoin Microsoft 365 account, and to any recipient, inside or outside Bowdoin, who receives an encrypted Bowdoin email message.

  • Encryption ensures that only the intended recipient can read the message and that no one else can read its contents.

Resolution

Send an encrypted email message

To send an encrypted message, add the word [encrypt] to the subject line. Include the square brackets [ ] around the word.


Read an encrypted email message

  1. When an encrypted email is sent, the recipient does not receive the message itself. Instead, the recipient receives a notification email stating that an encrypted message has been sent, similar to the example below.

    Notification email with subject '[encrypt]' showing instructions to open an encrypted message using a message.html attachment and sign in with a Bowdoin email.

    To open the actual message and any attachments, follow the instructions provided in the notification. Download and open the attachment. The attachment must be downloaded. If the attachment is opened directly without downloading, links are provided for mobile devices to download the app needed to open the encrypted attachment, but the next set of instructions will not be visible.

    Once the attachment is opened, additional instructions are provided.

    Microsoft 365 encrypted message notice with options to sign in or use a one-time passcode to view the message.

  2. If the recipient is a Bowdoin community member or is from an institution that uses Microsoft 365, select Sign In to sign in and view the message.

    Sign-in options for viewing an encrypted message: Microsoft account or work or school account, with a link for a one-time passcode.

  3. If the recipient is not a member of the Bowdoin community, select Use a one-time passcode. A single-use passcode is emailed to the recipient's email address, which is the same address used on the original message. The passcode is valid for 15 minutes only. Enter the passcode in the box provided on the previous web page.

    Microsoft 365 email showing a one-time passcode and instructions to use the code to view a protected message.

  4. Once authenticated, the original email message is displayed. The recipient can reply to, forward, or print the message. Any reply or forward of the message is also encrypted, along with all subsequent messages in the conversation.

    Outlook on the web showing a decrypted message from a Bowdoin sender to a recipient with the text: Test message.


Resolve an error when sending an encrypted message

Bowdoin has changed the service it uses to send encrypted email messages. Some staff may have an add-in installed in Outlook that adds an encrypt button. That button no longer works, and using it produces an error message similar to the one below.

Email error message stating a custom mail flow rule at bowdoin.onmicrosoft.com blocked delivery, with instructions for how to fix it.

To send the encrypted message, return to the original message, add [encrypt] to the subject line, and send it again.

Additional Help

If you need further assistance, you have several options:

  • Bowdoin Bot: Chat with Bowdoin Bot directly from any KB page for instant answers.
  • Phone: Call the Bowdoin College Service Desk at (207) 725-3030.
  • In person: Visit the Tech Hub in Smith Union during business hours.
  • Submit a ticket: Request assistance through the Service Catalog.

Details

Details

Article ID: 31524
Created
Wed 6/7/17 1:30 PM
Modified
Thu 7/30/26 3:27 PM