This guide walks you through enabling automatic email forwarding from your Outlook/Microsoft 365 mailbox to an external email address. Because external forwarding is a security-sensitive setting, it requires two steps: an admin must first enable it in the Microsoft Security Centre, and then you can configure it in your own mailbox settings.
Part 1: Admin – Enable External Forwarding in Microsoft Security Centre
This step must be completed by your IT administrator. If you are an end user, please pass this section to your IT team.
By default, Microsoft 365 blocks automatic forwarding to external addresses as an anti-spam and data-loss prevention measure. An admin needs to lift this restriction before users can forward externally.
Sign in to the Microsoft Defender portal at security.microsoft.com with a Global Administrator or Security Administrator account.
In the left-hand menu, go to Email & Collaboration → Policies & Rules → Threat policies.
Under Rules, select Anti-spam policies.
Click on the Anti-spam outbound policy (Default) (or the policy applied to your users).
In the policy flyout panel, scroll to the Automatic forwarding section and click Edit protection settings.
Under Automatic forwarding rules, change the setting from Automatic – System-controlled (or Off) to On – Forwarding is enabled.
Click Save.
Note: You can also create a custom outbound policy targeted at a specific group of users if you don't want to enable external forwarding for your entire organisation.
Part 2: User – Set Up Auto-Forwarding in Outlook
Once your administrator has enabled external forwarding, follow these steps to configure forwarding on your own mailbox.
Option A: Outlook on the Web (Recommended)
Sign in to your mailbox at outlook.office.com.
Click the Settings gear icon (top right corner).
Select View all Outlook settings at the bottom of the Settings panel.
Go to Mail → Forwarding.
Tick the checkbox Enable forwarding.
Enter the Caresquare forwarding email address located in the Settings dashboard in Caresquare.
(Optional) Tick Keep a copy of forwarded messages if you also want emails to remain in your Outlook inbox.
Click Save.
Option B: Classic Outlook Desktop App (Windows)
Open Outlook and go to File → Info → Manage Rules & Alerts.
On the Email Rules tab, click New Rule.
Under Start from a blank rule, select Apply rule on messages I receive and click Next.
Leave all conditions unticked (to apply to all incoming messages) and click Next. Confirm the prompt by clicking Yes.
Tick forward it to people or public group in the actions list.
In the rule description at the bottom, click the people or public group link and your Caresquare forwarding email, which can be found in the Settings dashboard in Caresquare. Click OK.
Click Next, add any exceptions if needed, then click Next again.
Give the rule a name (e.g., "Auto-forward to personal email") and tick Turn on this rule.
Click Finish, then Apply and OK.
Troubleshooting
Problem | Likely Cause | Fix |
"Forwarding failed" or emails not arriving | External forwarding not enabled by admin | Complete Part 1 above |
Setting not visible in Outlook on the Web | Policy not yet applied (can take up to 1 hour) | Wait and try again, or contact IT |
Forwarded emails going to spam | Recipient's spam filter flagging forwarded mail | Ask the recipient to whitelist your domain |
Forwarding loop warning | Destination address also forwards back | Use a different destination address |
Important Considerations
Security: Forwarding corporate email to an external address may conflict with your organisation's data handling policies. Check with your IT or compliance team before setting this up.
Scope: Forwarding applies to all incoming emails unless you use rules (Option B) to filter by sender, subject, or other criteria.
Disabling forwarding: To turn off forwarding, return to the same settings screen and untick Enable forwarding (Outlook on the Web) or delete/disable the rule (desktop app).