Hi @shannonm,
Welcome to Microsoft Q&A, and thank you very much for reaching out.
Based on your description, may I check whether the rule you created is server‑side or client‑side?
You can verify this by signing in to Outlook web > Settings > Mail > Rules and checking whether the rule appears there. If the rule exists in Outlook web, it is a server‑side rule.
If your inbox rules are server‑side rule, from my research, the recommended way to resolve this behavior is to recreate the rule directly in Outlook web, rather than in Outlook Classic.
To avoid any potential conflicts, please first delete the existing rules in Outlook Classic. It may be helpful to note what each rule does so you can recreate it accurately.
Next, create the same mail rule in Outlook on the web. Once created, the rule should automatically sync back to Outlook (Classic) and begin running as expected.
I hope this helps.
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