Freemail services provide email access for free to millions of accounts; however, to do so they have to keep their operations pretty lean.  One of the ways they keep things lean is by being extremely strict on their email filtering.  Any time an IP address on the internet sends more than a couple spammy messages, they simply start putting all email from that IP address into the Junk folder of their subscriber and leave it then up to their  subscribers to de-classify it as junk if they wish.
The challenge for the rest of the ISPs of the world is that if just a couple of their subscribers send unwanted messages to a freemail service, they run a risk of having all their subscribers blocked (or Junked) by that freemail service for a period of time.
Also, the SMTP protocol was never really designed to accommodate email forwarding plus spam filtering.  This really confuses the freemail services as to where the unwanted email is coming from.  If user joe@yourdomain.com forwards their email to joe@hotmail.com, here’s what happens.

  • Email from spammer@spammyplace.com arrives on our server for joe@yourdomain.com.
  • The email is forwarded to joe@hotmail.com per the subscriber’s request
  • Hotmail receives the email, and looks back only 1 hop to determine who this spammer is (in this case, they tag the server that joe@yourdomain.com is on) rather than the real originating server.
  • If this happens enough, hotmail will block all email from @yourdomain.com.  This one user who forwards their email just negatively affected all your other users when they marked the email fromspammer@spammyplace.com as Junk in their hotmail account.

The freemail providers have all begun recommending against forwarding email to their systems in this manner because it confuses their spam filters.  They instead have built in POP3 email checking into their systems so their subscribers can have the same functionality without the need to forward email.  Their subscribers still get all their email in their freemail inbox just as how it worked when email was previously forwarded.
To accommodate these changes at the freemail services, our systems will pop up warnings to subscribers when they attempt to forward email to a freemail service and recommend they setup an email account instead, and check it using the freemail service’s 3rd party pop3 mail checking feature.
Here’s some basic directions on how to setup that service for the major freemail providers.  For more in-depth directions or support on the process, the subscriber should contact the technical support department or help files at their freemail provider.

  • Outlook / Hotmail: Go to More Mail Settings, Your Email Accounts, Add a send-and-receive account.
  • Yahoo: Go to Mail Options, Mail Accounts, then click to Add a new account.
  • Gmail: Go to Settings, Accounts tab, then click ‘Add a POP3 mail account you own’