Hello Donna Thorvaldson,
Thank you for reaching out to Microsoft Q&A Forum!
I understand how frustrating it is when rules only work some of the time. Here are a few steps that you can try:
1. Check rule order and conflicts
- Go to Settings > View all Outlook settings > Mail > Rules.
- Make sure the rule to move messages from those contacts is at the top of the list. Rules run in order, and another rule may override it.
2. Match addresses exactly
- Sometimes emails come from an alias.
- Edit your rule so it covers the full email address, or add multiple variations.
3. Verify it applies to all message types
- If the rule only applies to “when the message arrives in the Inbox,” it may not catch messages that Outlook routes into Focused/Other automatically.
- Try setting the condition to “from…” without other restrictions.
4. Clear browser or client cache
- If you’re using Outlook.com, sign out, clear cookies/cache, and sign back in.
- If you’re using Outlook for Windows/Mac, recreate the rule inside the app instead of web, or vice versa, to confirm which side works better.
5. Re-create the rule
If it still behaves inconsistently, delete and re-create the rule fresh. A corrupted rule is a common cause of partial failures.
I hope this helps! Please feel free to let me know how it goes. Take care!
Warm regards
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