hotmail no longer redirects emails

Several conditions can stop Outlook.com/Hotmail redirect (Inbox) rules from working, even if they used to work before. Work through these checks in order:

1. Verify rules are configured as Redirect rules

• In Outlook.com / Outlook on the web:
  1. Select Settings (gear icon).
  2. Select Mail > Rules.
  3. Open each rule and confirm the action is Redirect to (not just Move to or Forward to), and that the Gmail address is correct.
  4. Ensure Stop processing more rules is set the way that is intended (usually enabled on the last rule in a chain, disabled on earlier ones).
  Steps to create/confirm a redirect rule are documented for Outlook.com/Outlook on the web:
  • Settings → Mail → Rules → Add new rule → condition (for example, "Apply to all messages" or "From" a specific address) → action Redirect to → Gmail address → Save.

2. Check mailbox size and limits

• If the mailbox is near or over its storage limit, forwarding/redirect rules may stop working until space is freed.
• Even when redirecting/forwarding, copies of messages stay in the mailbox (or Deleted Items if a delete action is added) and still count against the quota. If the limit is exceeded, sending/receiving and forwarding rules can fail until enough mail is deleted.

3. Check number of recipients in rules

• If any redirect/forward rule sends to multiple recipients, the number of individual addresses is limited. If the limit is exceeded, the rule will not work. In that case, reduce the number of recipients or redirect to a distribution/group address instead.

4. Confirm that the rules are not blocked by forwarding controls

• For work/school Microsoft 365 accounts, automatic forwarding to external recipients can be disabled by admin policies (outbound spam filter or remote domain settings). If this is the case, rules that forward/redirect to Gmail will not work and can generate nondelivery reports. Only an admin can change those policies.

5. Check that messages are not already auto-forwarded or looped

• If a message has already been forwarded/redirected once (for example, by another rule or another mailbox), Exchange Online enforces a loop-prevention limit. A message can only be automatically redirected/forwarded once; further automatic redirects/forwards for that message will not run.

6. Confirm the message type is supported

• Inbox rules will not forward/redirect:
  • Certain automatic replies.
  • Some delivery reports or message disposition notifications.
  • New/updated meeting requests marked Private. If the messages being tested are of these types, the behavior is by design.

7. Recreate rules cleanly

• Since new rules were already tried, ensure old/duplicate rules are removed and only the current intended rules remain under Settings → Mail → Rules.
• After changes, send a simple test message from the specific address to confirm whether it redirects and/or moves to the folder.

If, after checking all of the above, redirect rules still do not work and the account is a consumer Outlook.com/Hotmail account (not work/school), contact Outlook.com support from within the service, as some issues (such as backend bugs or account-specific problems) can only be fixed by support.

References:

• Use rules to automatically forward messages
• Diagnose Outlook Inbox rules that aren't working