Outlook.com encrypted email fails with “Internal Server Error: Object reference not set to an instance of an object”
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Anonymous
I have a Microsoft 365 Family subscription and cannot send encrypted email. When I try to send an encrypted message from Outlook.com (web) or the Outlook mobile app, I receive: “Internal Server Error: Object reference not set to an instance of an object.” This occurs consistently on: - Outlook.com web - Outlook mobile app What I’ve already confirmed: - Primary alias is an @outlook.com address - S/MIME is disabled - Issue reproduces across devices and browsers - This is not an app-specific issue Based on this behavior, this appears to be a server-side Outlook.com mailbox provisioning issue related to Purview Message Encryption / IRM. How can this be escalated to the Outlook.com service team so the mailbox encryption configuration can be re-provisioned?
Outlook | Web | Outlook.com | Email
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Anonymous
2026-03-07T12:29:50.3933333+00:00 -
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Chloe-V 6,155 Reputation points Microsoft External Staff Moderator2026-03-09T06:52:33.1866667+00:00 Hi Brandy,
To help review this further, please go to the Private Message section and provide the information I requested there. That information will help determine the appropriate next steps.
Thank you for your time and cooperation.
Since this is a public forum, we will hide your personal identifiable information, and I have sent that image of yours containing your personal identifiable information in a private message so we can work together to resolve the issue. Also, please check your private message in case you want to share another screenshot to avoid leaking your PII by click on the Private Message button as show below
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Chloe-V 6,155 Reputation points Microsoft External Staff Moderator
2026-03-03T07:49:10.74+00:00 Hi Brandy,
Thank you for reaching out to Microsoft Q&A forum.
Could you please help clarify the following so we can narrow this down further?
- Are you able to send emails successfully when encryption is not enabled, and does the behavior only occur when you select Encrypt?
- Does the same behavior occur when you send a test email to yourself or to external addresses such as Gmail or Yahoo?
- When the behavior occurs, does the page or app display any Request ID / Correlation ID / Technical details? If yes, please share them with me via private message.
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- Does this occur on Outlook.com on the web and the Outlook mobile app? Please include the browser, operating system, and app version (iOS / Android).
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.
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Anonymous
2026-03-07T12:32:31.51+00:00 Chloe---I can send unencrypted emails successfully. It only occurs when encrypt or use the do not forward feature. It occurs to test emails to myself and others. It has occurred with GMAIL and Outlook addresses.
It occurs on the Outlook.com/mobile/desktop version.
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