Comments on: False positive spam problem with hotmail

Question: False positive spam problem with hotmail

twiggy — Thu, 29 Sep 2005 14:32:37 -0800

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.

By: seawallrunner

seawallrunner — Thu, 29 Sep 2005 14:42:23 -0800

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.

By: SpecialK

SpecialK — Thu, 29 Sep 2005 15:08:07 -0800

What happens if you look up a reverse DNS record for mail server's name?

By: twiggy

twiggy — Thu, 29 Sep 2005 16:11:20 -0800

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...

By: Kickstart70

Kickstart70 — Thu, 29 Sep 2005 16:50:16 -0800

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.

By: I Love Tacos

I Love Tacos — Thu, 29 Sep 2005 16:55:18 -0800

Check all your DNS info with DNS Report.

By: devilsbrigade

devilsbrigade — Thu, 29 Sep 2005 17:27:36 -0800

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.

By: twiggy

twiggy — Thu, 29 Sep 2005 17:42:31 -0800

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.

By: Rhomboid

Rhomboid — Thu, 29 Sep 2005 19:34:02 -0800

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.

By: b1tr0t

b1tr0t — Thu, 29 Sep 2005 21:17:10 -0800

lots of good suggestions above, another possibility:

Someone else in your IP block is a spammer, and your entire IP-range is marked as such. You would be surprised how many "reputable" vendors sell to spammer.

By: twiggy

twiggy — Thu, 29 Sep 2005 22:06:05 -0800

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...

By: Rhomboid

Rhomboid — Fri, 30 Sep 2005 03:01:47 -0800

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.