Does anyone know how you avoid sending emails to hotmail going to spam?

6 points by immad ↗ HN

7 comments

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I have talked to a few other people and they have had similar problems, thought someone here might have a solution. Basically we are using Qmail to send emails out from our website (ruby on rails). Everything seems to be working except for hotmail, where they always go to spam.

We are using a hacky solution at the moment but that limits how many emails we can send, does someone have a good way around this, paying a small price per month wouldn't be too bad for a solution.

Register your server (the one sending email) with SenderID http://www.microsoft.com/mscorp/safety/technologies/senderid/overview.mspx which is an MS invention -- their record wizard is here: http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/

The rest of the world (at least those email servers that check for this stuff) uses SPF records.

This site http://www.openspf.org/ tells you how to setup SPF on your server.

sounds promising. We have SPF setup. Going to check out SenderID now. Thanks
I may have some information about this, but it's a little bit crude. It comes from Adam Curry's Daily Source Code podcast, when he was first setting up his startup Podshow and was having similar troubles (and not just with Hotmail -- all the webmail providers!).

Btw, the first thing I would do is get SenderID working. It will work with almost everything -- sendmail and postfix at least, so I'd bet that it works with qmail too.

According to what Adam says he found, you have to be registered with some sort of clearing house or all the webmail providers will drop you as spam. This is not senderid or spf. The only efficient way to be 'registered' is to purchase and appliance from a company for upwards of $80K. I think this includes configuring it with your domain info as well.

I wish my 'info' was not so vague. It comes from 1+ years ago, and Adam was never super-clear about specifics. It always sounded a little weird to me, but OTOH I do believe the webmail providers would do this. Apparently, it's done in the name of anti-spam, but the spammers are allowed to buy these appliances, so it's really about milking more money from emailers, and maybe about squeezing out the little guy.

I'm hoping someone out there can clear some of this up, because it's a problem we all potentially face (if it's real).

Make sure you have reverse DNS that points at your mail server ( eg mail.your-site.com ) , not just the root domain ( eg not your-site.com ). A lack of reverse DNS or an automatically generated reverse DNS ( eg isp-1-0-0-127.isp-site.net ) won't do.
I do not think that there is "one way" to fix this (if there were, then it would be easy for spammers to go straight to inboxes)

Reverse DNS (ip mail domain)

SPF Record

Sender ID

3rd party verification (goodmail systems is one example linked from aol's spam abuse) - they are $400. 80k sounds like a little bit too much

Apply to be "whitelisted" at each specific provider (http://help.yahoo.com/fast/help/us/mail/cgi_bulkmail is yahoos, aol has one)

Switch MTAs (postfix, sendmail, qmail) - try alternating

Make sure your headers make sense and are valid (reply-to,return-path, from, message-id, etc)

Finally, send email people actually want. It seems that the systems are somewhat automated (aol is for sure) to reject mail if a certain % of users flag it as spam.

Are you sure it's not due to how your email headers and content look? I had to remove my X-Mailer "Mail-Sender" and supply a proper address with a name before Hotmail would stop putting the emails into spam.