Hi Naveed,
Greatly appreciate your time sharing the details about your situation.
Based on your sharing, you have already resolved the situation: delivery confirmation, no hidden rules detected, sign-ins behavior is consistent, and switching to "Do not group messages" setting does fix the issue. The problem now is to find the root cause, whether the preference change was exposed to Purview as an auditable event or stayed as an Outlook/OWA mailbox preference update that is not consistently surfaced.
For you to receive the best possible assistance, I strongly recommend submitting a support ticket directly to Microsoft for further investigation. This route ensures you can contact a support agent, who can conduct a remote session to review the issue in detail, validate backend configurations and run any required synchronization or diagnostic tools. If necessary, he/she can help escalate this situation to a specialized/high-tier team for more in‑depth analysis and resolution.
I genuinely wish I could directly review the backend systems to diagnose and resolve this issue for you. However, as a forum user, I can only provide general guidance, sharing applicable resources, and directing you to the appropriate support channels so you can work with the right team to investigate further. That said, this option is the most effective approach I can provide so you can receive the most correct, specialized support for this situation.
To create a support ticket:
- Go to Microsoft 365 Admin Center > Support > Help & Support
- Turn off the "Support Assistant" feature.
- Use the keyword "Support" to quickly bypass automated suggestions > Select Contact Support.
- In the ticket description, please clearly describe the issue, including any error messages and the steps you’ve already tried. You can also attach screenshots or screen recordings.
- Additionally, sharing your preferred contact times may help the support team handle the case more efficiently.
Thank you for your understanding and I truly hope your concern will be resolved soon.
Note: Please follow the steps in the forum documentation to enable e-mail notifications if you want to receive the related email notification for this thread.