Using classic Outlook for Windows in business environments
Hi @Hotard Nedal
Thank you for posting your question in the Microsoft Q&A forum.
After doing some research, I notice there are few cases like yours.
If some Outlook rules only work when you click "Run now", they’re likely client-only rules (e.g., moving mail to PST/local folders, using custom scripts, or "on this computer only"), too complex, or blocked by higher-priority rules. To fix this, edit them to run server-side (avoid local-only actions), simplify conditions, and check the rule order so nothing prevents them from triggering automatically.
Some rules work automatically only if they are server-based. Rules created only on the client side (such as Outlook installed on your PC) may require you to run them manually.
I found this way that might help, you could try is removing all rules both the client and server level, then start from scratch.
If you have too many rules to delete manually, you can use this to clear them all at once.
Firstly, press Win + R to open Run dialog. In the Run dialog box, enter the Outlook.exe /cleanrules in the Open box, and click the OK button.
(Note: If there are more than one account in your profile, all rules in all accounts will be deleted.)
Then from here, please re-create your rules.
Please try and let me know if it works for you.
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