I have has this issue for a while and its starting to cause problems so I need a workaround.
The problem is I use Gmail to send emails using my MSN account. When I send the email to multiple recipients which have different domains it sends the email to all recipients that many times. So if I send email to 3 recipients whose emails are email@example.com, firstname.lastname@example.org, email@example.com, each user will get the same email 3 times. If I send the email to 3 recipients on the same domain it works as it should. When this issue happens, in Gmail only one email is being sent, but in outlook.com multiple emails show as sent.
This forum post on Google shows the exact problem another user is having.
The result of that conversation is this quote:
Microsoft are not following the guidelines set in RFC5321, so Google might choose not to implement a work around for Microsoft's behaviour even though Yahoo apparently has done that.
So my question is this: Is there any workaround for this issue? If not what other options do I have? I want to use Gmail/Inbox but my MSN email is on my business cards and has to be used as the From address.
I also have a GoDaddy email and I tried to set a identity for my MSN but it only works using the GoDaddy web interface. I was hoping it would work through Gmail using SMTP.
Is there another service out there to do what I need?