unable to send encrypted email from Outlook

Question

I am unable to send encrypted email from Outlook for Windows or Outlook web. I was able to send encrypted email last month. The Outlook technical support team for Windows said that the problem is on the server end.

Answer 1

Welcome Leonard Edelman,

I understand how frustrating it can be when you are unable to send encrypted emails from Outlook for Windows and Outlook on the web, even though this was working previously. 

Before we proceed further, I would like to narrow this down to better understand the scenario: 

• Are you using a personal Microsoft account or a work or school account when sending encrypted emails? 
• Does the issue occur with all recipients or only when sending to external recipients outside your organization? 

In the meantime, you can try the workaround steps to see:  

Step 1: Sign out of Outlook and sign back in, then try sending an encrypted email again to refresh the account session 

Step 2: Check whether email encryption is enabled for your account:  

• For Outlook on the web, go to Settings, then Mail, and check Message encryption 

Step 3: Verify that your Outlook app is fully up to date by checking for updates and restarting the application afterward 

Step 4: Try sending an encrypted email from a different browser or from an InPrivate or Incognito window to rule out browser-related issues. 

Step 5: Temporarily disable any third-party add-ins in Outlook and test if encryption works without them 

I hope this information helps resolve your issue. If you have any further questions, please don’t hesitate to contact me again in this thread. 

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