Dear @Penny Maraglia,
As a moderator, I do not have the tools to investigate your specific account directly because this is a user-to-user support forum. Our role is limited to providing technical support on reported issues, requests, or ideas. However, I will try my best to support you as clearly as possible.
At this time, the new Outlook for Windows does not support a combined view that automatically keeps flagged messages pinned at the top while still showing all other emails below in date order (the way classic Outlook can).
That said, there are a few practical workarounds you can use to get close to the workflow you want:
Pin the most critical emails/conversations
If your main goal is to keep key items always visible at the top, you can Pin specific messages or conversations so they remain at the top of your message list, and unpin them when you are done.
Add “Flagged messages” to Favorites for one‑click access
While this will not merge flagged and unflagged mail into one combined list, adding Flagged messages to Favorites makes it much faster to switch between your Inbox (sorted by date) and your flagged items without having to search each time.
I completely understand this is not the ideal experience, and I appreciate your patience while Microsoft continues improving the new Outlook. If you would like, you can raise a feedback so this specific “flagged on top + rest by date” capability is formally captured as a feature request.
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