some redirected emails do not arrive

Question

The thing is that if I send an email through WEBMAIL from ******@administracionadalid.com to ******@hotmail.com, it is received in HOTMAIL, but the forwards that should arrive when ******@administracionadalid.com receives an email and it is supposed to be forwarded to ******@hotmail.com are not being received. We have checked by adding a Gmail account to the forwarding rules of ******@administracionadalid.com, and it does arrive there, and also another different Hotmail account, and the forwards arrive, but to ******@hotmail.com they do not arrive.

Answer 1

Hello,

Forwarded mail often fails SPF at the final destination, because Microsoft sees the forwarding server IP, not the original sender’s sending server.

If the original message has no valid DKIM, then DMARC alignment can fail after forwarding.

I just reviewed the SPF for your domain, looks like it has some error.

You might want to get rid of \n at the end.

Answer 2

For this scenario, the forwarding from the administracionadalid.com mailbox is working in general (messages reach Gmail and another Hotmail account), so the issue is specific to delivery into the target Hotmail mailbox. The context covers how forwarding/redirect rules work and common reasons why they fail, but not a case where only one specific Outlook.com/Hotmail mailbox fails while others succeed. The following are the supported checks and actions:

1. Confirm the type of rule in the source mailbox
   • In Outlook on the web or Outlook.com for the administracionadalid.com mailbox, go to Settings → Mail → Rules.
   • Verify that the rule is configured to Forward to or Redirect to the Hotmail address and that it is applied to the expected messages (for example, Apply to all messages).
   • If using redirect, remember: redirected messages appear from the original sender; replies go to the original sender, not the forwarding mailbox.
   • If using forward, messages appear as forwarded from the administracionadalid.com account; replies go back there.
2. Check that forwarding/redirect rules are functioning overall
   • Since messages are successfully forwarded to Gmail and another Hotmail account, the rule itself is functioning and the source server is sending the messages out.
3. Check for rule/forwarding limits (on the source side)
   • If the rule sends to multiple recipients, ensure the number of individual recipients does not exceed the Exchange Online Inbox rule limit of 10. If it does, create a distribution group or Microsoft 365 group, add the recipients there, and set the rule to send only to that group.
4. Check for mailbox-level forwarding conflicts (source mailbox)
   • If the administracionadalid.com mailbox also has mailbox-level forwarding configured (in addition to Inbox rules), this can interfere with redirect rules. Use Exchange Online PowerShell to check:

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

   • If mailbox forwarding is enabled and redirect rules are used, disable mailbox forwarding so Inbox redirect rules can work:

          Set-Mailbox <user ID> -DeliverToMailboxAndForward $False
     

5. Check the destination Hotmail mailbox for blocking or filtering
   • In the destination Hotmail/Outlook.com mailbox, sign in and go to Settings → Options or Mail → Blocked senders / Block and allow.
   • Remove the administracionadalid.com address or domain from Blocked senders if present.
   • Also review any rules in that Hotmail mailbox (Settings → Mail → Rules) that might move or delete messages from administracionadalid.com.
6. Check Junk/Deleted Items and mailbox quota on the destination Hotmail account
   • Forwarded/redirected messages may be delivered to Junk Email or Deleted Items.
   • If the Hotmail mailbox is over its storage limit, new messages (including forwarded ones) may be rejected or not delivered until space is freed.
7. Consider external forwarding controls and remote-domain settings (admin level)
   • If this is a Microsoft 365/Exchange Online tenant, an admin should verify:
     • Outbound spam policies are not blocking automatic external forwarding to this specific domain. If automatic external forwarding is disabled, rules that forward externally will not work and can generate NDRs.
     • The remote-domain configuration does not have AutoForwardEnabled set to False for the Hotmail/Outlook.com domain. If so, enable automatic forwarding for that remote domain using Set-RemoteDomain.

If all of the above checks are clean and forwarding still works to other destinations but not to this one Hotmail mailbox, the remaining step is to focus on that specific Hotmail account’s filtering (rules, blocked senders, junk handling, and quota) and, if necessary, have the owner of that Hotmail account contact Microsoft support via the Outlook.com support channel for mailbox-specific investigation.

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References:

• Use rules to automatically forward messages
• Diagnose Outlook Inbox rules that aren't working
• Where are my email messages or calendar events in Mail and Calendar for Windows 10?