E-mail - SMTP communication problems with other servers

Posted on 2008-10-21
Last Modified: 2013-12-18
Lately, I have noticed problems with e-mailing external customers.  It doesn't happen to every external e-mail account, just a select few which is odd I thought.  The problem is that we attempt to send an e-mail, and almost immediately it comes back with

            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
    #5.5.0 smtp;554 Transaction Failed Spam Message not queued

It's almost like it hits my Exchange box, and comes back with that immediately.  Other times, when a message has failed and at least went out to the recipient e-mail server there is a bit of a delay until we receive an undeliverable message.  I did a little bit of digger deeping, and found that my name server and MX record is still being hosted by an old ISP while the IP address actually belongs to another provider.  I'm thinking this could be the problem?  It's been this way for years though, never had problems like this before.  IF this is the problem, do I just call my old ISP who is hosting my MX record and move it to my new ISP?  Also, change my registrar and move the name servers to my new ISP as well?  If i'm way off here, let me know!  That's why I'm asking the questions here before I just do it  :)

Question by:jmchristy
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LVL 16

Expert Comment

by:Carol Chisholm
ID: 22766357
There are all sorts of reasons, but you could make a good start by getting your DNS entries (forward and reverse) to match the actual servers you are using (in and out).
LVL 26

Expert Comment

ID: 22766675
Call your new isp and get them to setup the domain and all associated records. Once they have that setup, go to your registrar and change the nameservers from the old ISP to the new ISP.  After a few days with everything working, you can let your old ISP know to remove your domain.

Author Comment

ID: 22776746
It just seems odd that I can send e-mail to about 95% of my customers, but the other 5% are getting kicked back to me with that error 554.  So from what you guys are saying, it's not a problem on there end it's definitely with my setup?  I asked a couple of guys and they said it doesn't matter who hosted my DNS and that it didn't have to be my carrier.
LVL 26

Accepted Solution

jar3817 earned 500 total points
ID: 22776843
" #5.5.0 smtp;554 Transaction Failed Spam Message not queued"

SMTP errors can be rather difficult to interpret, I'm reading this one as "your message was caught as spam and is rejected." The question is simply why was it caught as spam. It could be your DNS (but if 95% is ok, it's not DNS), it could be blacklists or it could be the content. Some people have stricter filters than others.

My wife sent an email to her brother at work with a url of something funny. The message bounced as being spam. I told her to write a paragraph or just add some more content to the body of the email and send the same URL again. Second time it went through no problem. People are getting sick and tired of spam and are tightening the filters down more and more. I would contact the people who bounce your email and get the reason why. They're really the only ones who can tell you why.
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Author Comment

ID: 22776919
That's the thing, these e-mails that are getting rejected are simply text, maybe with a picture attachment but nothing major.  I am in contact with these few companies which are rejected my e-mail but haven't heard back from anyone yet.  I'm contacting them thru my hotmail account to avoid and un-necessary blocking.

So as far as anyone can tell, there's no configuration error on my end and it's getting rejected on the other end as spam?
LVL 26

Expert Comment

ID: 22777059
If you can deliver to 95% of recipients, your setup is probably fine. I would call these companies on the phone and ask to speak with the person in charge of email.

Author Comment

ID: 22811533
The problem ended up being that a company called TrustedSource had us flagged as a malicious e-mailer.  I recently renewed my domain, and later that day we were flagged.  They claimed that "dns spam" is what got us set to a malicious e-mailer status, so I asked them to move me back to at least neutral and then e-mail started working again within 4 hours.

Author Closing Comment

ID: 31508219
While it wasn't the exact solution, it helped point me in the right direction that it wasn't a problem within my system.

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