False positive spam problem with hotmail

September 29, 2005 2:32 PM

Despite plenty of googling, and even email with Microsoft's support - I cannot seem to solve my problem. I'm wondering if perhaps any of my fellow geeks have had this problem: I run a web/email server of my own, colocated in a highly reputable facility. For some reason, Hotmail views any email coming from my box as spam, and tosses it in a junk folder. I've done all the checks to make sure I don't have an open spam relay problem, etc. I've checked all the blacklists I can think of -- I'm not on any of them.

Are any of you having your legitimately sent email relegated to Hotmail's SPAM coffers? Hotmail says they'd love to help me, but they use Brightmail by Symantec, and it is they who need to help me. Symantec, however, has not responded to repeated emails/phone calls.

I've even done what I need to do (I think) to follow Microsoft's Sender ID program - yet still my email is relegated to spam folders. Personal email - no attachments, nothing out of the ordinary.

posted by twiggy to Computers & Internet (10 answers total)

yes, unfortunately, hotmail is known to do this... my mail to friends' hotmail addresses was relegated to Junk and vice versa. Solution - I switched to gmail

So you are not alone with this twiggy. Now, as far as geekhelp to fix this, sorry I can't help you but I hope that someone will.
posted by seawallrunner at 2:42 PM on September 29, 2005

What happens if you look up a reverse DNS record for mail server's name?
posted by SpecialK at 3:08 PM on September 29, 2005

Response by poster: There is a reverse DNS record, but I host mail for many, many domains, so it does not match mail.[anydomain].com if that's what you mean...
posted by twiggy at 4:11 PM on September 29, 2005

In your logs (assuming you have decent full logs) is a message that looks something like this example for AOL (the only one I could find at the moment):

status=deferred (host mailin-03.mx.aol.com[64.12.137.249] said: 421-: (DYN:T1) http://postmaster.info.aol.com/errors/421dynt1.html 421 SERVICE NOT AVAILABLE (in reply to end of DATA command))

That page has lots of info, including a form you can fill out to be freed to send to AOL addresses. I know this info is specific to AOL, but I'm sure I've seen very similar for hotmail.
posted by Kickstart70 at 4:50 PM on September 29, 2005

Check all your DNS info with DNS Report.
posted by I Love Tacos at 4:55 PM on September 29, 2005

Part of the SMTP protocol demands that reverse DNS requests = the incoming server. Many, many servers don't care about this, but I run into it often enough that I bugged my host for a seperate IP for RDNS. Like it or not, its still part of the protocol.
posted by devilsbrigade at 5:27 PM on September 29, 2005

Response by poster: My info with DNS Report looks good. As far as the logs - I get no error messages or warnings from hotmail that my message is spam. It's just silently placed in hotmail's junk folder.
posted by twiggy at 5:42 PM on September 29, 2005

The reverse DNS only has to match the HELO, it doesn't have to have anything to do with the envelope-from, header-from, or any other address in the email. And it's not really a strict requirement, but some servers use it as a sign of spam. I don't think this is your problem.

I suggest getting a full copy of the message with headers after it's delivered and run that through SpamAssassin. See if any of its numerous tests flag anything. It would also help immensely if we had a sample to work with.
posted by Rhomboid at 7:34 PM on September 29, 2005

Response by poster: Rhomboid: Thank you for your response. Unfortunately, the ONLY place this is happening is Hotmail. I run spamassassin myself, and it doesn't find anything funky with my emails.

If you think you might be able to help, email me at steve AT openingbands DOT com and I'll send you an email so you can look for yourself. I'm pretty sure I'm compliant with everything Hotmail asks.


b1tr0t: definitely a possibility... but I would think I'd be on some blacklists other than hotmail if that were the case... especially because this has been going on for nearly a year now...


Thank you to all who've replied thus far...
posted by twiggy at 10:06 PM on September 29, 2005

It could very well be that some admin at hotmail added by hand the /16 (or /24 or whatever) that you happen to be in to some internal filtering rule. If that is the case then it sounds like getting in contact with them is the only way to deal with it.

If it's business-critical then you could probably find a very cheap smarthost service that you would use only for stuff destined to @hotmail.com.
posted by Rhomboid at 3:01 AM on September 30, 2005