How to fix automatic forwarding rule not working

Hello Patrick Haagensen

Thank you for reaching out to Microsoft Q&A Forum.

I understand how frustrating it is when forwarding's not working and Gmail messages aren’t reaching your Hotmail inbox.

Before going further, could you please confirm whether you’ve already tried the steps in the Q&A Assist reply above? If yes, let me know which step didn’t work so we can narrow this down.

Based on what you described, here are a few additional checks that you could try:

1. Check built-in forwarding (not Inbox Rules)

Instead of relying only on Inbox rules:

• Sign in at Outlook on the web
• Go to Settings > Mail > Forwarding
• Enable forwarding and enter your Gmail address
• Choose “Keep a copy of forwarded messages” if needed
• Save changes and test with a new incoming email

2. Make sure Gmail isn’t blocking Outlook

Since Gmail emails are not reaching Hotmail either, this points to filtering on both sides

• In the same setting in Outlook: Go to Settings > Mail > Junk email
• Ensure your Gmail address/domain is not under Blocked senders and domains
• Add it to Safe senders and domains

In Gmail:

• Check Spam and All Mail
• Add your Hotmail address to Gmail contacts
• Check for bounce or error messages

3. Disable any conflicting rules

If multiple rules exist, especially ones that move or delete mail, they can prevent auto-forwarding from triggering.

• Temporarily disable all rules
• Test forwarding again with a new email
• Send a plain-text message (no attachments/links) to your Hotmail account and see if it's arrived

Please let me know which steps you’ve already tried and what the result is, and I’ll help you take the next appropriate steps. Thank you for your understanding and patience!

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To troubleshoot the issue with your automatic forwarding rule not working in your Hotmail account, consider the following steps:

1. Check Mailbox Forwarding Settings: Ensure that mailbox forwarding is enabled correctly. You can run the following PowerShell cmdlet in Exchange Online PowerShell to check if forwarding is set up properly:

      Get-Mailbox <user ID> | FL ForwardingAddress,ForwardingSmtpAddress,DeliverToMailboxAndForward
   

   If forwarding is enabled, Inbox rules that redirect messages may not work as expected.
2. Review Inbox Rule Configuration: Make sure that your Inbox rule for forwarding is configured correctly. Check if the rule exceeds the limit of 10 individual recipients, as this could prevent it from functioning properly. If it does, consider creating a distribution group to manage the recipients more effectively.
3. Check for Conflicting Rules: If there are multiple Inbox rules, ensure that they are not conflicting with each other. An incoming message may be redirected by another rule, which could lead to unexpected behavior.
4. Examine Spam Filter Settings: Verify whether the outbound spam filter settings are blocking automatic forwarding to external recipients. If the filter is set to block such forwarding, it will prevent your rule from working as intended. You can check the settings in the outbound spam filter policy.
5. Test the Rule: After making adjustments, test the rule by sending a new email to your Hotmail account to see if it forwards to your Gmail account as expected.

If you continue to experience issues, you may want to consult the Microsoft documentation for further troubleshooting steps or reach out to their support for assistance.

References:

• Diagnose Outlook Inbox rules that aren't working
• Control automatic external email forwarding from cloud mailboxes

Good day Patrick Haagensen, I hope you're well. May I know if you've got any chance to check my reply? If you have any further updates on this issue, please feel free to post back. I'm happy to help you.