My email provider is Hotmail. I tried this and i was able to book a flight/resend receipts to new email successfully. I even tested to auto fwd to my original email and that worked too so it doesnt seem like my personal hotmail is blocking incoming emails from Southwest domain.

Switching the email to a temp one and then switching back to my original email actually fixed an error I was receiving on Southwests website when attempting to reset password.

• We are unable to validate this account with the information provided. Please double check to make sure all the information is correct and matches the information in your account. If you continue to have difficulties, please contact a Southwest Airlines Customer Representative for assistance at 1-800-I-FLY-SWA (1-800-435-9792).

So now Southwest recognizes my original email is linked to my account but still no emails come through.