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One of my customers (annoyingly) uses HotMail for his primary email address. A lot of the time, my emails to him get returned undeliverable due an over-zealous spam filter.

My email is from my own company domain, signed with a valid certificate and the domain supports Sender-ID and SPF.

My belief is that the provider of my domain's email hosting is using the same SMTP server for multiple customers, some of which are abusing it and hence getting the server blacklisted by HotMail.

Is there anything more I can do with this setup? Or am I gonna have to head over to ServerFault to find a provider of dedicated email servers (don't want full web hosting and all that crap, just POP3/IMAP & SMTP that works) ?

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Not convinced this should have been moved to Web Apps, since I was sending to a Hotmail user not *from Hotmail, but whatever.... – Rob Cowell Jan 21 '11 at 9:05
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migrated from superuser.com Jan 20 '11 at 17:48

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3 Answers

up vote 3 down vote

The only thing I can think of that doesn't involve changing hosting is to get your customers to add your e-mail address to their white list.

I know it's not ideal, but I see it on a lot of mailing list mails for this very reason.

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I guess that solves it for one customer - if I don't get a better generic solution (i.e. a fix for all hotmail recipients), I'll mark yours as the accepted answer – Rob Cowell Sep 11 '09 at 9:39
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up vote 3 down vote

Even with SenderID and DKIM both properly configured and tested, we can't get our Stack Overflow mails through to hotmail.com email addresses -- they regularly go in the spam folder.

Apparently hotmail is a tough nut to crack...

The autoresponder at check-auth@verifier.port25.com is a great resource for this. Send an email to it with a valid reply address, and it'll tell you what isn't configured properly.

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As for "they regularly go in the spam folder": any idea if similar messages go into the spam folder for some users, but not for others? Or do you think that it is the body that yields the spam score (as the headers are probably fine)? – Arjan Jan 8 '10 at 17:57
Hmm. I will have to test that, but the content is quite innocuous and isn't flagged for spam via the check-auth@verifier.port25.com either .. (it does a spam/ham test as well) – Jeff Atwood♦ Jan 8 '10 at 19:22
Could it be that too many Hotmail users have hit the "Mark this as spam" (or equivalent, I'm not a hotmail user so don't know the exact wording) because they're too lazy to correct their email preferences? – Rob Cowell Jan 10 '10 at 12:24
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up vote 2 down vote

You might have a look at MSN's Sender Solutions which describes (quote)

a suite of services to help senders improve their deliverability to Windows Live Hotmail consumers

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Have emailed postmaster, have set up SPF and Sender-ID. I draw the line at being accredited by a third party (Sender Score Certified Email) as I don't believe I should have to pay out extra money just to be email to send emails. I've jumped through enough hoops getting signing and SPF/SenderID set up already. – Rob Cowell Sep 11 '09 at 9:30
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