Rules Just Don't Work

This is indeed frustrating. Outlook rules can be finicky, and it's disappointing to hear that you're experiencing issues with what should be a straightforward task. Let's troubleshoot this step-by-step:

1. Rule order: Make sure this rule is at the top of your rule list. Rules are processed in order, so if there's a more general rule above it, that might be interfering.
2. Rule creation: Try recreating the rule from scratch. Sometimes, rules can become corrupted.
3. Specific steps:
   • Start with "Apply this rule after the message arrives"
   • Add condition "sent to [your specific address]"
   • Add condition "with attachment"
   • Set action "forward it to [alternate address]"
4. Test the rule: Send test emails to yourself, some with attachments and some without, to verify the rule's behavior.
5. Client vs. Server: Ensure you're creating a server-side rule rather than a client-side rule, especially if you're using Outlook on multiple devices.
6. Clear cache: Try clearing your Outlook cache and restarting the application.
7. Update Outlook: Ensure you're running the latest version of Outlook 365.

If none of these steps work, it might be worth considering alternative approaches:

1. Use Power Automate (formerly Microsoft Flow) to create a more robust email handling workflow.
2. Create a separate folder and use a rule to move all emails to this address into that folder. Then set up a second rule that only applies to that folder for forwarding emails with attachments.
3. Contact Microsoft Support directly, as this could be a bug in their system.

Thanks

win32diskimager