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Networking DNS, Samba, IP masquerading, etc. related questions.

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  #1  
Old 03-23-2007, 08:06 AM
xrx's Avatar
xrx xrx is offline
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Exclamation Mail being tagged as spam + Hotmail deletes half of it

(I do know that this has been mentioned before, but no one talked about anything they have done to avoid being marked as spam. Found out about a very unusual "spam" _deleting_ technique used by hotmail as well, read on)

Okay, this is getting to the point of being _extremely_ annoying. I handle mail servers for other people, but decided on getting my own domain name and server for my needs. The mail server I handle for others usually send mail to non-free mail accounts, but for me, most of my friends and the people I work with have hotmail/yahoo/gmail accounts.

I've done almost everything I could to avoid being marked as spam:

- Static IP + Not an open relay: I'm not new to mail servers, and I double checked that it is not an open relay with online tools. Its a secured postfix server, and every package on the system is updated daily. It's a brand new Xen VPS too, with a dedicated IP address. It's only been live for about a week.

- IP not in any blacklist: Not listed in any spam ip database.

- Reverse DNS setup properly: The reverse lookup matches the domain that is sending the mail perfectly.

- SPF records setup and working: I've checked my SPF records with three online utilities, two of which are e-mail address you can e-mail, which auto-responds with the results of an SPF check. It passed everything.

I sent test mails to accounts in three of the major free mail providers:

- Yahoo
It still placed my mail in the bulk folder. The headers did not give any hints on why it was tagged as spam. Fine, I looked into the yahoo documents, and found out that they're pushing they're own sender verification technique called DomainKeys, which lead to DKIM. I didn't like it much; although the idea sounded good, they seems to be the only company going for it, and that too the older DomainKeys proposal and it seemed odd that I would have to modify my postfix for yahoo alone. But I was desperate, and I slept late learning about it and implementing it in my DNS and postfix server.
After waiting for the DNS changes to get propagated, I found out that it still moved my mail to the bulk folder. I checked with their recommended verifier to make sure my settings was okay, and got an automated e-mail with:
Code:
==========================================================
Summary of Results
==========================================================
mail-from check:   pass
PRA check:         pass
DomainKeys check:  pass
The test message even had a "Yahoo! DomainKeys has confirmed that this message was sent by xxxx.com" message. I checked the settings to make sure there isn't a rule saying people that are not in my contacts would be moved to the bulk folder, but I was sure that such a rule did not exist, because I received viagra spam in my damned yahoo inbox!! That didn't get moved into my bulk folder, oh no, just mail from my law abiding postfix mail server. That viagra mail had major things wrong with it:
- IP Listed in 7 blacklists
- Reverse DNS lookup points to p508CDBA3.dip.t-dialin.net, clearly a dynamic ip address
- Domain was clearly spoofed
- No DomainKeys (but its optional)

I have absolutely no idea what that person did to avoid the bulk folder.

-Hotmail
Oh, this is the most interesting bit. Note that I implemented openSPF, which _seemed_ to be finally accepted by microsoft (read about the senderid problem), at least according to the results of microsoft-recommended (port25.com) senderid checkers. Even the online senderid wizard from microsoft said my records was fine. I was surprised that every mail I sent to the hotmail account just disappeared. This was one of my e-mails:
Code:
What's up?


-xrx
It was _not_ in my junk, or my inbox, or anywhere. Then I looked into my postfix logs (BTW, thats not my real e-mail address, but its something like it):
Code:
Mar 22 10:39:15 xxxxxx postfix/smtp[2731]: 4A67024650A: to=<microsoft_sucks@hotmail.com>, relay=mx3.hotmail.com[65.54.244.72]:25, delay=0.65, delays=0.05/0.03/0.25/0.32, dsn=2.0.0, status=sent (250  <4602A35F.4030309@xxxxx.com> Queued mail for delivery)
Mar 22 10:39:15 xxxxxx postfix/qmgr[2469]: 4A67024650A: removed
That's it. No news after that. No sign of clear rejection. The hotmail account never does receive the mail.
However, after much research on google, someone (there was a bigger discussion, but I lost the link) claimed that if you include the link http://join.msn.com, the mail will get through successfully. Yes, in the junk, but at least it would send. I tried it out:
Code:
What's up?


-xrx

----------------
Please do not http://join.msn.com
Code:
Mar 23 05:20:16 xxxxxx postfix/smtp[15830]: C060B24651A: to=<microsoft_sucks@hotmail.com>, relay=mx1.hotmail.com[65.54.244.136]:25, delay=0.61, delays=0.04/0/0.27/0.29, dsn=2.0.0, status=sent (250  <4603AA1C.3010505@xxxxx.com> Queued mail for delivery)
Mar 23 05:20:16 xxxxxx postfix/qmgr[11224]: C060B24651A: removed
It worked, I received it in the junk folder. However, after a lot of further testing, it seems almost very unpredictable, and wasn't clearly linked with including the MSN link. As of now, I'm not exactly sure what triggers it to delete some of the e-mails silently. All of the accepted e-mails were plain-text, but there was some plain text e-mails that was rejected as well. Here are some test messages.


- GMail
Google did not tag my mail as spam, goes ahead directly to the inbox as expected.
3 other mail providers accepted my mail without any trouble too.

Now, at this stage, there seems to be only one last way of solving this, asking them to add me to their whitelist. Yahoo has a nice form to fill that might work, I will try it out. But for microsoft hotmail, the only way for them to consider adding me to their whitelist, since I'm a "non-profit" mail-server handler, is to pay them $400.

Needless to say, I'm very annoyed by the whole situation, and would really appreciate any feedback or ideas.
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  #2  
Old 03-23-2007, 11:58 AM
je_fro's Avatar
je_fro je_fro is offline
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Hotmail is dead....tell everyone to only use it as their "throwaway" inbox.
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Old 03-23-2007, 12:50 PM
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cybertron cybertron is offline
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That sucks dude. I hate e-mail filters that don't tell you what they're doing or give you the opportunity to give the thumbs up to a message anyway, but I'm not surprised that Microsoft's would be so broken worse than most.
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  #4  
Old 03-26-2007, 10:27 AM
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xrx xrx is offline
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Update: got a message from Yahoo after filling in the form and answering their questionnaire that they sent me (which assumed I'm a business wanting to have a mailing list, never mind). My mail doesn't seem to be tagged as spam from Yahoo anymore (although they stated that I wasn't whitelisted, but that they made "appropriate changes" to their database, which I assume means a negative score added after the usual spam detection). My question on what triggered the spam filter, although asked politely twice, went unanswered. I suppose they wouldn't want to give any hints if I were to be or talk to a possible spammer.

The hotmail problem is still unsolved.
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