Forwarding is not working at all

Dear Spencer Chesman - Promis Care,

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

Before we proceed with full troubleshooting, I’d like to ask a few quick questions to help us scope down the issue:

Which account are you using for forwarding? Is it a personal Outlook account or a business/enterprise Microsoft 365 account?

Have you tried forwarding using the Outlook desktop or mobile app?

Could you please send us a screenshot of your current forwarding settings?

Are you forwarding to an internal address (within your organization) or an external one? Some organizations restrict external forwarding for security reasons.

Is this happening in a personal mailbox or a shared mailbox?

And just to make sure you go on right process, do you fill the email you want to auto forward and click Save:

Also, just to clarify:

Forwarding in Outlook automatically sends emails that you receive from others to the address you’ve set. It does not forward emails that you write and send to others.

So, if someone sends you an email, Outlook will forward that message to your configured forwarding address. But emails you compose and send out yourself will not be forwarded automatically. Here’s a helpful point to remember.

In the meantime, after you check all my question and information above, and the issue still persists for you, I’ve reviewed similar cases and kindly shared a list of advanced solutions below. If any of this overlap with what you’ve already tried, please feel free to skip them.

1. Check Organizational Policies

If you use a business account, ask your IT admin to help you check, you can give them this reference: Configuring and controlling external email forwarding in Microsoft 365 - Microsoft Defender for Office 365 | Microsoft Learn

2. Review Rules and Filters

• Go to Settings > Mail > Rules
• Delete or adjust any rules that may interfere with forwarding

3. Clear Browser Cache or Try Another Browser

• Use updated browsers like Edge or Chrome
• Clear cache using Ctrl + Shift + Del

4. Check Junk and Blocked Lists

• Add the forwarding address to Safe Senders
• Remove any blocked domains that may interfere

5. Check Mailbox Quota

• Ensure your mailbox isn’t full
• Clean up Deleted Items and Junk Email

Please reply with the requested details so we can assist you further. We’re committed to resolving this quickly.

Warm Regards.

If this response has been helpful, we kindly encourage you to mark it as Accepted Answer. Doing so will assist other users with similar questions in finding accurate and timely solutions more easily.

We appreciate your participation in the community and look forward to supporting you further.

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Dear Spencer Chesman - Promis Care,

Thank you for the detailed explanation and it’s very helpful, your assumption is absolutely on point.

Since the two business accounts are on separate and didn't connect Microsoft 365 plans, it’s possibly that organizational or admin-level policies are preventing email forwarding between them. These restrictions are commonly in place to protect data and maintain compliance across tenants. You're doing the right thing by having your admin check the configuration.

Also, your idea of showing a clear message like "your organization does not allow forwarding" is excellent. It would definitely improve the user experience and reduce confusion when forwarding silently fails. But as you mentioned that account is non-connected Microsoft plans, so Microsoft have no permission with that. So, my strongest recommendation is to discuss with your admin, contact directly to your organization email service and ask them to check if they can adjust help you with this. 

In the meantime, I also recommend marking an Accepted Answer for now. Doing so will pin the thread to the top, making it easier for others to find when searching with related keywords. It helps highlight the discussion for users who might benefit from it, and of course, the thread remains open for anyone to join and share their thoughts. 

That way, it can also be pinned and gain more visibility. I’d be happy to vote for it, and I’m sure other users with similar concerns would appreciate the chance to support it too.

Thanks again for raising this important topic!