Can someone help me figure out why i was able to send encrypted emails 3 weeks ago and now i cannot?

Question

I have a Microsoft 365 Personal account for 3 years. I have been sending encrypted emails from the web for over two years and now i cannot. I have been told i need to send from the desktop, that doesn't work, I've had people remote in and no one can fix it. I have put in countless tickets and they always tell me do open another and they will get me to the "dedicated team" but i can never reach them. Microsoft support cannot help me and they keep sending me to Microsoft teams who are just giving me the run around. This has been going on for 3 weeks. Yesterday Harsch told me a manager would be calling me and no one ever did. I am so frustrated and losing time and money. Can someone please help?

Answer 1

Hi CRISTINE DUNNING

I understand you have a Microsoft 365 Personal subscription and encryption from Outlook.com (web) stopped working, and desktop attempts plus multiple support tickets have not resolved it. Please confirm:  

• Are you failing on Outlook.com web when you do: New message > Options > Encrypt?  
• What is the exact error message text, and do you see any Request/Correlation ID when it fails? 

I would love to hear from you soon. Have a nice day!

Answer 2

Based on the documented behavior, there are three main areas to check when encrypted mail suddenly stops working after having worked previously.

1. Confirm the encryption feature is still available for the account

• Microsoft Purview Message Encryption (Office 365 Message Encryption) depends on:
  • A Microsoft 365 subscription that supports message encryption.
  • Correct tenant configuration.
  • A valid license assigned to the signed‑in account.
• If any of these changed (subscription downgraded, tenant misconfigured, or license removed), symptoms include:
  • Inability to send encrypted messages.
  • Missing Encrypt button in Outlook on the web or desktop.
• Have the subscription and license status checked for the Microsoft account being used to sign in. If the account no longer has a license that includes Microsoft Purview Message Encryption, encryption will stop working even if it worked before.

2. Use the supported way to encrypt from Outlook (desktop)

• For classic Outlook on Windows, there is a known issue if encryption is applied via File → Encrypt.
• When that path is used, recipients may be unable to open “Encrypt Only” messages, and it can cause encryption issues.
• Instead, when composing a message in classic Outlook:
  1. Open a new email.
  2. Go to the Options ribbon.
  3. Select Encrypt.
  4. Choose Encrypt or Do Not Forward.
• This is the supported method for sending encrypted messages with a Microsoft 365 Personal or Family subscription.

3. Basic troubleshooting for sending/opening encrypted mail

• If encrypted messages cannot be opened or sent from the web:
  • Ensure the device is connected to the internet (encryption policies and keys are validated online).
  • If recipients report they cannot open messages, verify that the encrypted email contains the Read the message link; if it does not, the sender must resend the message.

If the Encrypt option has disappeared from Outlook on the web and desktop, or encryption fails even when using Options → Encrypt, this strongly indicates a subscription, tenant, or license issue as described above. In that case, the next step is to have support verify that the Microsoft 365 Personal subscription is active and that the account is still licensed for Microsoft Purview Message Encryption.

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References:

• Resolve Microsoft Purview Message Encryption issues
• Classic Outlook recipients are unable to open "Encrypt Only" emails
• Troubleshoot Office 365 message encryption
• Send encrypted messages with a Microsoft 365 personal or family subscription