qmail unable to send email to certain domains

I'm having an issue where qmail is unable to send to certain domains, leaving them in the queue for about a week before returning the messages with this mailer-daemon error:

Connected to xxx.xxx.xxx.xxx but connection died. (#4.4.2)
I'm not going to try again; this message has been in the queue too long.

95% of my messages send out just fine, right now it's only about 5 domains that I cannot send to, but the list seems to be slowly growing.

Here's my server info:
" Media Temple (dv) server
" Plesk server software
" Linux
" I use a shared IP with about 25 of my clients

After doing a lot of research on this, the only answer that I've come across is that my domain (or IP) is on a blacklist. I've used quite a few tools to find out if this is the case, but thus far I'm not on any lists...

I've resorted to using my gmail account to send mail to these certain domains, but unless I check the mail queue every time I send a message (not practical) it takes a week for the me know if someone received the message...

Thanks in advance,
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Daniel McAllisterConnect With a Mentor President, IT4SOHO, LLCCommented:
There are a number of reasons why your messages may be being blocked... for example, I had a devil of a time getting my system to send to yahoo.com for a while because my QMail implementation of DomainKeys wasn't compatible with theirs... in the end, they placed my static IP address on a "white list" and I am no longer being blocked.

So, if you've already been to http://www.mxtoolbox.com and come up clean (don't worry if their reverse-DNS lookup fails the first time, re-check it and it should be OK -- assuming your reverse-DNS is valid -- their DNS client times out too quickly for many reverse DNS lookups), then contact the recipient's mail admin and ask to see what they say they see in their log files. They may be able to help you find the issue.

Of course, you should also look in your own SMTP log files (location is dependent upon how you installed it, but it may be in /var/log/qmail/smtp/current or /supervise/smtp/log/current or any of a dozen or more locations).

As for joeyfm's suggestion you get an additional IP address, assuming you're already on a STATIC IP address and the reverse DNS entry is not "generic", and you're not on any blacklists... then there is no cause to add or change the IP address of your server.

SPAM costs ISPs (large and small) billions of dollars in wasted bandwidth, storage, and frustration from users. The fight continues, and each time a "new" fix comes along (like DomainKeys above), there is a "learning curve" for the mail admins who haven't adopted it yet...

Good luck! And please post back here with your results!

This may or may not help, but if you get your internet service providor to issue a new dedicated ip address to the line that the server is using.
hope this helps.
spigotdesignAuthor Commented:

I'm wondering if you're right, and that's my only recourse. I'll give it a try and report back.

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spigotdesignAuthor Commented:
Well, switching IP addresses didn't solve the issue, as itsoho pointed out.

I've been on the phone with a couple of the hosts for accounts I'm unable to send to, as well as my own host and I'm stuck in the middle of a he-says-she-says scenario.

I've found a workaround for now, which is to use my ISP's SMTP server to send mail to these recipients.
Not ideal, but at least I know they're getting there.

Daniel McAllisterPresident, IT4SOHO, LLCCommented:
The receiving sites are unable to say why their mail host refused (or dropped) your connection?

Sounds like front-line tech support -- not particularly helpful...

Maybe try sending a note to postmaster@domain.com? (Believe it or not, a message to postmaster@yahoo.com got me a REAL answer from a REAL tech!)

Good luck! (Did you try all the tests at mxtoolbox?)

spigotdesignAuthor Commented:

I did try all the tools at mxtoolbox, and I was pleased to see that my domain/IP are clean. I'm really glad this isn't a blacklist issue.

The strangest thing is that it's so random (and rare, thankfully), so I'm tending to believe my hosting company over the others, and that the connection is being blocked for some reason.

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