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You have set up a forwarder so mail to [email protected] arrives in your Gmail or Outlook.com inbox, and it is being blocked or filed as spam.

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Why forwarding fails

When our server forwards a message, it is sending mail it did not originate. To the receiving provider that looks like exactly what a spammer does, and it fails the sender checks that the original message would have passed. Gmail and Outlook.com both treat forwarded mail with suspicion as a result. It also means any spam sent to your address gets forwarded too, and that counts against our sending reputation rather than the original sender’s. See E-mail forwarders.
One case that looks like a failure but is not. If [email protected] forwards to [email protected], and you then send from [email protected] to [email protected], the message will not appear back in your Gmail inbox.That is deliberate — it prevents email loops. Nothing is broken.

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The fix: let the provider collect the mail instead

Rather than pushing mail out with a forwarder, have Gmail or Outlook.com pull it in over IMAP or POP. The message arrives directly from our server as the original, passes the usual checks, and lands in the inbox. Turn off the forwarder first, or you will get duplicates.

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Gmail

Gmail collects from another mailbox using POP. See Setting up Gmail to access your email account. If you also want to send as your own address from Gmail, Gmail will ask you to verify it.

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Outlook.com

  1. Turn off any forwarders pointing at the Outlook.com address.
  2. Log in to Outlook.com, click the settings icon, then View all Outlook settings.
  3. Go to Sync email → Connected accounts → Other email accounts.
  4. Under Advanced settings, tick Manually configure account settings, and click OK.
  5. Enter the email address you want to collect from.
  6. For User name, enter the full email address, for example [email protected].
  7. Enter the mailbox password.
  8. Choose where messages should be stored — a new folder, or your existing Outlook folders.
  9. Choose IMAP or POP. IMAP keeps mail on the server and is usually the better choice — see Introduction to email protocols.
  10. For the incoming server, enter mail.example.com, replacing example.com with your domain. The port fills in automatically: 993 for IMAP, 995 for POP.
  11. For POP only: tick Leave a copy of messages on the server if you want to keep them. Without it, Outlook downloads and removes them.
  12. Set Authentication to Basic and Encryption to SSL.
  13. To send as this address from Outlook, choose Send email using your provider’s server and enter mail.example.com as the outgoing server. Otherwise choose to send using the Outlook.com server.
  14. Click OK. The account appears under Manage your connected accounts, and the mail appears under its own entry in the left sidebar.
This applies to any destination, not just these two. Any provider that offers to collect mail from another account will work better than a forwarder. If yours does not, the more reliable option is to add the mailbox to a mail app directly — see Add your email to your phone and desktop.