Hi @Jennifer Burke,
Thank you for posting your question in the Microsoft Q&A forum.
I can understand how inconvenient it can be when your flagged emails disappeared. This behavior can happen because in the new Outlook, only flagged emails from your primary mailbox appear in Microsoft To Do. Flags set in shared mailboxes or shared folders do not sync to To Do, so they won’t show up in the Flagged email list. To Do also loads only the most recent 100 flagged messages from the last 30 days, which means older or very large numbers of flagged items may not appear. Since the classic Tasks module has been replaced by To Do in the new Outlook, flagged emails won’t show in the old Tasks view either, they only appear in To Do’s Flagged email list or through Outlook search and filters.
Here are a few steps that often help:
1/ Open Microsoft To Do and turn on “Flagged email”:
In To Do, select your profile picture > Settings > ensure Flagged email is On. Then select Help & feedback > Sync to refresh.

Reference: Using Microsoft To Do with flagged email from Outlook
2/ Use Outlook’s built‑in filter:
In New Outlook, click Filter (above the message list) and choose Flagged to list all flagged messages.
3/ Search for flagged messages if Filter isn’t available:
In Outlook’s search box, use IsFlagged:yes to return flagged mail across folders. You can scope the search to a specific folder if needed.
Reference: How to search in Outlook
4/ Confirm the message location:
If the missing items were moved to another account, shared mailbox, or Online Archive, move them back to your primary mailbox and re‑flag if necessary, only primary‑mailbox items sync to To Do’s flagged list.
5/ Re‑sync To Do if it looks stale:
- Sign out from both Outlook on the web (outlook.office.com) and Microsoft To Do (to-do.office.com).
- Close all browser tabs related to Microsoft 365 to ensure there are no active cached sessions.
- Open your browser settings and clear temporary internet files, cookies, and cached images.
- For accuracy, choose the option to delete cached data for at least the last 7 days.
- Once cleared, close and reopen the browser fully (do not just refresh).

6/ Submit feedback:
If you've tried all the above steps and the issue still persists, I highly recommend submitting a suggestion directly from Outlook by navigating to: Outlook (new) · Community portal. This is the most effective way to ensure your voice reaches the product team and can be considered for future improvements.

Once you've submitted your feedback, feel free to share the link here in the comments. I’ll be happy to upvote it to help bring more visibility.
Additionally, since many other users have expressed similar concerns but may not know where to submit feedback, if my response has helped you better understand the situation and guided you toward a possible next step, please mark it as the “Accepted Answer.” Your action will help pin this post to the top, making it easier for others in the community who are experiencing the same issue to find your feedback and support it.
Thank you again for your time and for raising this important usability concern. If you have any questions or need further support, please don’t hesitate to reach out at any time.
I look forward to your update.
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