Classic Outlook Contacts that have an X509 S/MIME certificate added to the Global Address List can no longer be edited with Operation Failed error

Last Updated: May 28, 2025

ISSUE

After a contact is saved with classic Outlook from the Address book (Add to Contact option from the contact Dialog), an EBA modifies the PidLidEmail1OriginalEntryId property of the contact. The property is changed from the service side and gets applied whether Outlook is open or not. 

For contacts that have an X509 (S/MIME) certificate added to the Global Address List (GAL), the property changes will cause Outlook to show an “Operation Failed” error when trying to modify the local contact.

STATUS: INVESTIGATING

This issue has been escalated to the service team for contacts for investigation. We will update this topic when we know this will be fixed.   

WORKAROUND 

If you urgently need to work around the issue, you can remove the certificate from the local Contact if you need to modify the contact.

Additional Resources

How to Configure S/MIME in Office 365

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See Also

Fixes or workarounds for recent issues in classic Outlook for Windows