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Re:What Mailchimp does to make sure emails get delivered by NathanOsullivan on Sunday July 17, 2016 @04:40AM (#12109487)
Yes, hotmail will in some instances accept mail at SMTP level and then silently discard it. You cannot even request de-listing.
Re:What Mailchimp does to make sure emails get delivered by xyzzy123 on Sunday July 17, 2016 @06:59AM (#12109727)
I had to deal with delivery issues to hotmail (few years ago though) and despite a few hoops, found them pretty reasonable to deal with. Some tools here: https://mail.live.com/mail/services.aspx and https://mail.live.com/mail/troubleshooting.aspx