unable to send encrypted emails on my laptop or ipad

Question

Hello, i am a foster Carer & need to be able to send encrypted emails, i used to be able to perform this task but not anymore, what do i need to do to be able to perform this task on both my laptop & ipad.

Thank you.

Answer 1

To send encrypted email again on both laptop and iPad, two things are required:

1. A qualifying Microsoft 365 subscription that includes Outlook encryption.
2. The correct encryption method set up and selected when composing mail.

Follow these steps on each device.

1. Confirm subscription and account

Encryption in Outlook (including Outlook.com accounts) requires a qualifying Microsoft 365 subscription such as Microsoft 365 Family or Microsoft 365 Personal.

If that subscription has lapsed or the account in Outlook is not the same one with the subscription, encryption options will not be available.

2. Using Microsoft 365 encryption (recommended for your scenario)

This is the simplest option if using Outlook.com or a Microsoft 365 mailbox.

On the laptop (classic Outlook / new Outlook / Outlook.com in a browser)

1. Start a new email.
2. Go to the Options ribbon.
3. Select Encrypt.
4. Choose one of:
   • Encrypt – message stays encrypted and does not leave Microsoft 365.
   • Do Not Forward – message is encrypted and cannot be copied or forwarded.
5. Compose and send the email.

If encryption was previously set from File > Encrypt in classic Outlook and recipients could not open messages, switch to using Options > Encrypt instead.

On iPad (Outlook for iOS)

1. Open Outlook for iOS and start a new email.
2. With a Microsoft 365 Family or Personal subscription on that account, encryption options are available for the message.
3. Choose Encrypt or Do Not Forward for the message before sending.

This keeps the message encrypted within Microsoft 365 and is designed for scenarios where the recipient’s email provider may not be secure.

3. Using S/MIME encryption (certificate-based, if that’s what was used before)

If encryption was previously done with S/MIME certificates:

• Encryption requires the recipient’s public key.
• For internal recipients (same email domain), their public key is stored in the Global Address List (GAL) and Outlook should retrieve it automatically when there is connectivity.
• For external recipients (different domain), a signed email must be exchanged first:
  1. Ask the recipient to send a digitally signed email.
  2. Install the certificate from that signed email.
  3. After that, encrypted emails can be sent to that recipient.

If encryption fails, it usually means the recipient’s public key is missing and needs to be obtained as above.

4. If encryption options disappeared after an update

If encryption stopped working after a recent Outlook update on the laptop and recipients cannot open “Encrypt Only” emails:

• Use Options > Encrypt instead of File > Encrypt when composing.
• If still broken and the environment allows it, reverting Office to a prior build that does not have the issue is another option, as documented, but this should be done only by someone comfortable managing Office builds.

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References:

• Send encrypted messages with a Microsoft 365 personal or family subscription
• Send S/MIME or Microsoft Purview encrypted emails in Outlook
• Why can't I encrypt?
• Learn about securing and protecting email messages in Outlook
• Classic Outlook recipients are unable to open "Encrypt Only" emails