Why are my Outlook items that are flagged, stay marked as flags after I clear them?

Hello, 

Thank you for reaching out to Microsoft Community. We're happy to support you with your concern. 

We're sorry that you're experiencing this issue for over a year now. We sincerely apologize and understand about the inconvenience that this may have caused you in such a long period of time. 

This issue is most commonly caused by sync lag or operation order conflicts in Classic Outlook: 

• Flag status is stored server-side (especially with Exchange/Office 365). If you clear the flag and immediately move the message, Outlook may:
• Sync the move faster than the flag-clear,
• The server sees the moved item as still flagged (from older status), and it pushes that flag back to the client (you see the flag “reappear”).

In resolving this issue, we kindly ask you to try some workarounds and see if it's helpful in eliminating the problem: 

1. **Clear the flag after you move the message:**This avoids the race condition between the two sync events.

• Move the email to the destination folder.
• Go to that folder.
• Clear the flag there.

If you prefer clearing first: 

• After clearing the flag, wait at least 10–15 seconds before moving the message.
• This gives Outlook time to sync the flag-cleared state to the server before the move occurs.

1. Delete Outlook Cache and OST Cache

• Close Outlook > press Windows + G and type %LOCALAPPDATA%\Microsoft\Outlook\ > delete the RoamCache folder.
• Do it again with Close Outlook > press Windows + G and type %LOCALAPPDATA%\Microsoft\Outlook\ > find your .ost file and delete it (Outlook will recreate it from the server when reopen)

1. Test in Outlook Web App (OWA):

Visit https://outlook.office.com and try your workflow there. If OWA doesn’t re-flag items, it confirms this is a local Outlook sync issue, not server rules or add-ins. 

1. Double-check and make sure no Quick Steps or rules are re-flagging messages.
2. Temporarily disable any **third-party Outlook add-ins:**Go to File > Options > Add-ins and disable any third-party add-ins.
3. Check if your OST file is large (>10GB), performance/sync issues can increase at that size.

Please understand that the initial response may not resolve your case directly but you can try workaround and update us if it helps resolve your concern. If anything still doesn't work right please feel free to let us know and we will keep assisting you. 

Best regards,   
Hendrix-C – MSFT | Microsoft Community Support Specialist

Hi Hendrix,

Sorry for the late reply.. After trying all these troubleshooting steps, the issue still persisted but the one thing that seems to have been the culprit was the "Rules" that were set in Outlook. I found a bunch of duplicate and redundant rules that were set that were telling Outlook to send messages all over the place and some that were set to re-send newly received emails back to the inbox. I deleted a ton of duplicate and redundant rules and I'm going to see if that's what was causing the issue but I'm confident that you mentioning that is source of my problem.

I'll have to wait and see but I appreciate your help. Thank you so much!

Hi Hendrix, thanks for the reply and helpful information. I'm going to try this when I get some time this week.

Hello,

Are there any updates on this issue? Have you resolved the issue well yet? Any updates would be greatly appreciated.

Kind regards,

Hendrix-C - MSFT | Microsoft Community Support Specialist