Email Delivery Errors

100 pts.
Application security
Current threats
human factors
Instant Messaging
Microsoft Exchange
Secure Coding
Hello All, Someone is having problems sending emails to us which did not exist before. Our email server (Unix based) did not list his domain as spam according to our email technician. Also for troubleshooting purposes i've asked him to send to my hotmail account which resulted in the same manor not receiving. After several attempts i received an email both on my hotmail and company accounts, emails sent before were test emails, no attachements. We have no limitation on attachments sent or received. Each company belongs to a different ISP. What could be the problem? What approach should i take to troubleshoot this problem. The following are the error messages he received ---************To Hotmail Account****************--- The attached message had PERMANENT fatal delivery errors! After one or more unsuccessful delivery attempts the attached message has been removed from the mail queue on this server. The number and frequency of delivery attempts are determined by local configuration parameters. YOUR MESSAGE WAS NOT DELIVERED TO ONE OR MORE RECIPIENTS! Failed address: : Message contains [1] file attachments ---*******************************************--- ---************To Company Account*************--- The attached message had transient non-fatal delivery errors THIS IS A WARNING MESSAGE ONLY - YOU DO NOT NEED TO RESEND YOUR MESSAGE! This server is configured to automatically retry delivery at configured intervals. Subsequent attempts to deliver this message are pending. Failed address: myemail@companydomain --- Session Transcript --- Wed 2007-01-24 11:06:15: Parsing Message <xxxxxxxxxxxxxxxxxxpd50000000621.msg> Wed 2007-01-24 11:06:15: From: hisemail@companyemail Wed 2007-01-24 11:06:15: To: myemail@companydomain Wed 2007-01-24 11:06:15: Subject: FW: : Egyption Law Wed 2007-01-24 11:06:15: Message-ID: <002101c73f84$a234f100$3af0e2c3@IMADIDS> Wed 2007-01-24 11:06:15: MX-record resolution of [companyEmailServer] in progress (DNS Server: Wed 2007-01-24 11:06:19: Name server has no records of the requested type for that domain Wed 2007-01-24 11:06:19: Attempting SMTP connection to [companyEmailServer : 25] Wed 2007-01-24 11:06:19: A-record resolution of [companyEmailServer] in progress (DNS Server: Wed 2007-01-24 11:06:19: D=companyEmailServer TTL=(106) A=[companyEmailServer] Wed 2007-01-24 11:06:19: Attempting SMTP connection to [companyEmailServer : 25] Wed 2007-01-24 11:06:19: Waiting for socket connection... Wed 2007-01-24 11:06:19: Socket connection established ( : 1112 -> companyEmailServer : 25) Wed 2007-01-24 11:06:19: Waiting for protocol initiation... Wed 2007-01-24 11:06:49: 30 second wait for protocol timeout exceeded. Wed 2007-01-24 11:06:49: This message is 71 minutes old; it has 0 minutes left in this queue Wed 2007-01-24 11:06:49: Primary queue lifetime exceeded; message placed in retry queue --- End Transcript --- : Message contains [1] file attachments ---*******************************************--- Thank You

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The first log hasn’t any info about the reason for rejecting message.

The second one simply points to companyEmailServer has not an MX record in the Name Server’s domain list.

I would try to ping companyEmailServer from the sender’s computer and, if successful, then try to open a telnet session from sender’s computer to company’s.

Hope it will help.

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  • petkoa
    Hi maryam82, If you have no trouble receiving mail from other people/networks, then the problem is hardly related to your DNS server configuration. Your correspondent also had problems reaching servers, though log in this case is very scarce... May be your correspondent have transient (ISP/backbone/etc related) problems reaching DNS servers on the internet, or have some problems with own resolver - e.g. dropping UDP packets on the firewall? The latter could happen on a stateful firewall because of long timeouts which lead to expiration of the expectation for the UDP "connection" (yes, UDP is connectionless, but stateful packet inspection on the firewall treats it in a manner similar to TCP connections) BR, Petko
    3,140 pointsBadges:
  • PDMeat
    It sounds like his mail server is complaining that when it looks up your email domain for MXs, it finds none. This can best be troubleshot using and look up your domain for MX records. Also, make sure that you have valid PTR records for all A records (and only ONE PTR per A record is allowed in SMTP) of your email host MXs. If you don't have a valid PTR and A record to back up your MX, many email servers will refuse your message and you should get an NDR to that effect, though not in every case. If you are having problems sending email from your co to hotmail, it's liekly there is a problem with something in your MX, A or PTR records for email. Keep in mind that many large organizations particulalrly, Hotmail, AOL, etc have their own Blacklists and they don't necessarily care what the public RBL's say about you. It's quite possible that, for exmaple, if you have a wrong or no PTR record for your MX/A record, hotmail will blacklist you without warning and you may not show up in any public RBL. If you know how to telnet into a mail server on port 25 from your mail server, you'll see the error's show up in the telnet session usually. There should be an error in your UNIX (sendmail?) SMTP logs if your logging level is on and working properly. Good luck.
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  • Maryam82
    Dear All, Thank You for all your replies. Our email server can not be pinged from outside because of the firewall settings. Only SMTP and POP3 are allowed. Using, I noticed that we do not have PTR records. But if this issue maybe causing a problem shouldn?t other companies face the same problem when sending us emails not a particular company? Our Institute has no problem sending to hotmail, it is the other company. After several attempts from his side I received the emails he is sending on my Institute account. Also he is facing problems receiving from us therefore I send emails to his hotmail account. It is more likely as you said, Petkoa, ISP problems, we both are on different ISPs. The problem still exsists. It is just that no changes where made on both sides, previously no problems occured. Thanks in advance for your help.
    100 pointsBadges:
  • Bermuda
    The DNS server that your correspondent is trying to use to resolve your smtp/domain name is which is in Kuwait. I don't know where you or your correspondent are based - is Kuwait halfway round the world ? The reason I ask is two-fold... it's possible your correspondents configured gateway for his outmail is sending you on a wild goose-chase (ie not using the shortest route for next hop to his ISPs DNS server (which is obviously likely to be very close to where his system is). It is vaguely possible that the Kuwaiti DNS server has not updated properly / anyway has the wrong IP address (if any) for you. It may not effect any other mail he sends to anyone else. On a slightly different tack... Is the DNS setting he uses actually set at his mail server or is it derived from the gateway his server connects to? Not very helpful but check if going via Kuwait is anything like a short(-ish) route.
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  • Maryam82
    Hi all, Well we are both located in Kuwait. and the DNS ( belongs to his ISP Qualitynet. I will contact him and check how his network settings are? Further more, i asked him to send me an email from his account to my Institute account. The email he sent is queued in a "remote queue", also other emails are queue in different queues. But only the email sent to me was queued in that particular queue. Does that indicate that his mail server is having problems connecting to our mail server or is it a general network problem, for example he needs to check his cable, IP settings, etc? Also, strangely before that happened i received emails from him and when i asked him to try again the queue problem occured. He has no problem receiving from us on his mail server, at the time my mail were queue i sent him and he immediately received them.
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