can't send a reply to an encrypted email

Question

I can send a new email with encryption but I can't send a reply to an email with encryption from my outlook address. I used to be able to until the last but one update my PC had.

I pay for this privilege and need it to send emails for work purposes which have confidential information. Can you please tell me how to fix this.

Answer 1

If you are unable to send a reply to an encrypted email in Outlook, there are several potential causes and solutions you can consider:

1. Check Your Digital ID: Ensure that your digital ID (certificate) is properly set up and trusted by the recipient's email system. If your digital ID is not trusted, you won't be able to encrypt messages.
2. Update Outlook: Sometimes, issues arise after updates. Ensure that you are using the latest version of Outlook. If the problem started after an update, check if there are any subsequent updates or patches that address this issue.
3. Certificate Issues: Verify that your certificate is valid and not expired. You can check this in the Microsoft Certificate Manager tool (certmrg.msc).
4. S/MIME Settings: Ensure that your S/MIME settings in Outlook are correctly configured. You may need to reconfigure your S/MIME settings if they were altered during the update.
5. Contact Support: If the issue persists, consider reaching out to Microsoft support for assistance, especially since this is impacting your work-related communications.

By following these steps, you should be able to troubleshoot and potentially resolve the issue with replying to encrypted emails.

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References:

• Error when sending S/MIME encrypted mails from OWA: Outlook Web Access could not find your digital ID for encryption
• Resolve Microsoft Purview Message Encryption issues

Answer 2

Hi @Tracey J Collier
Thank you for posting your question in Microsoft Q&A. 

We understand that you are experiencing an issue when replying to an encrypted email after updating your PC. 

To help address your issue more effectively, could you please provide additional information for the following questions: 

What is your current Outlook version, and is your account type (business/personal)? 

When you reply to the encrypted email, do you receive any decline message or does it simply not to send without a message? 

Based on my research, you could try replying to the encrypted email using Outlook Web Access (OWA). This approach can sometimes help avoid issues when responding to encrypted messages in desktop applications. 

You can refer via: Error replying to encrypted emails from Outlook Desktop - Microsoft Support 

Please understand that our initial reply may not always immediately resolve the issue. However, with your help and more detailed information, we can work together to find a solution. 

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