smtp cannot send to hotmail e-mail

Hi there,

My website shopping cart on windows 2003 with smtp cannot send email to all hotmail email address recently. But send all other email address is ok(for example, yahoo, gmail......). I don't  know what happend. My email server no any problem. and I test to sent to hotmail with outlook also is ok.
I just attached the error message below. I really appreciate if can get any help from here.

errer message:
The attached message had transient non-fatal delivery errors


This server is configured to automatically retry delivery at configured
intervals.  Subsequent attempts to deliver this message are pending.

Failed address:

--- Session Transcript ---
 Thu 2005-12-29 17:04:48: Parsing Message <xxxxxxxxxxxxxxxxxxxxxxxx\pd50000067089.msg>
 Thu 2005-12-29 17:04:48: From:
 Thu 2005-12-29 17:04:48: To:
 Thu 2005-12-29 17:04:48: Subject: phone Card   Order Number  93231
 Thu 2005-12-29 17:04:48: Message-ID: <000601c60ce8$8dcf0ae0$0dc6dad8@etalkbb>
 Thu 2005-12-29 17:04:48: MX-record resolution of [] in progress (DNS Server:
 Thu 2005-12-29 17:04:48: *  P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:04:48: *  P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:04:48: *  P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:04:48: *  P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:04:48: Attempting MX: P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:04:48: Attempting SMTP connection to [ : 25]
 Thu 2005-12-29 17:04:48: Waiting for socket connection...
 Thu 2005-12-29 17:05:09: Winsock Error 10060 The connection timed out.
 Thu 2005-12-29 17:05:09: Attempting MX: P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:05:09: Attempting SMTP connection to [ : 25]
 Thu 2005-12-29 17:05:09: Waiting for socket connection...
 Thu 2005-12-29 17:05:30: Winsock Error 10060 The connection timed out.
 Thu 2005-12-29 17:05:30: Attempting MX: P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:05:30: Attempting SMTP connection to [ : 25]
 Thu 2005-12-29 17:05:30: Waiting for socket connection...
 Thu 2005-12-29 17:05:51: Winsock Error 10060 The connection timed out.
 Thu 2005-12-29 17:05:51: Attempting MX: P=005 TTL=(39) MX=[] {}
 Thu 2005-12-29 17:05:51: Attempting SMTP connection to [ : 25]
 Thu 2005-12-29 17:05:51: Waiting for socket connection...
 Thu 2005-12-29 17:06:12: Winsock Error 10060 The connection timed out.
 Thu 2005-12-29 17:06:12: This message is 71 minutes old; it has 0 minutes left in this queue
 Thu 2005-12-29 17:06:12: Primary queue lifetime exceeded; message placed in retry queue
--- End Transcript ---
: Message contains [1] file attachments
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Greeetings  fortalk,

 If you have a look at this microsoft KB article it would help you to traceout the root cause of your problem

You can try to  exclude DNS from the logical chain and see if it's the problem, a good
workaround is to create an SMTP connector for the "" SMTP address
space, and specify Hotmail's MX servers as smart hosts for this connector

Hope this helps

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His DNS works, your network connection is working and attempting to send via port 25.  What kind of email server are you running?  It sounds like it is trying to send HELO instead of EHLO and the hotmail server can't figure out what your server is saying.

or, you've been black listed.
fortalkAuthor Commented:
Hi there,

Thanks for your feedback.
1. My email server is ok to send or receive email to or from hotmail. I can use outlook and webmail, all is fine. Only my webserver with smtp cdoys to send to hotmail cannot go through. If hotmail block my domain, why I can send with outlook or from webbase?
2. I use MDaemon email server. I don't know why my shopping cart only cannot send to hotmail. It also  doesn't work with Jmail to hotmail from my webserver. All other email address no any problem.

I really appreciate if can get your any help again. Happy New year,

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Bradley FoxLAN/WAN Systems AdministratorCommented:
You have not been blacklisted because if you were you wouldn't be albe to send from outlook.  Also hotmail understands helo, you can easily test this with telnet, which I just did.

What I did notice that the dns resolver you have for [] {} will not allow me to telnet to it on port 25.  This address is either down or is setup for sending mail only and is not listening on 25 to recieve.  If you nslookup you will get 4 addresses.  I was able to telnet in on 3 of the 4 on port 25.  I did not test mx2, mx3, or mx4 but I think it may be the same issue.

I would either contact hotmail to see if they are in fact having issues (that's a laugh, microsoft actually respond to anything) or just set a mx record for hotmail in your DNS using the good IP addresses.

Hope this helps!
fortalkAuthor Commented:
Hi there,

I contact hotmail tech support and our internet provider. but our email server still cannot send email to all hotmail address. To all other email is fine.  I just attached the information that I got from hotmail tech support below:


 When your mail server attempts to resolve “”, it is your DNS server that then tells your MTA what the IP’s are.  If the DNS server is properly updated, then you should be able to route to one of many active Hotmail IP addresses.

 Note that most mail clients allow you to manually point your mail server to a given IP address.  While not a long-term solution, routing your mail server directly to one of our active IP addresses should reenable your communication to MSN/Hotmail.

 The best solution, however, is to ensure that your DNS servers are properly updated with the current MX/IP information that I provided earlier.

Thank you,

 MSN Hotmail Domain Support
From: Support []
Sent: Friday, January 06, 2006 5:25 PM
To: GEST HM Inbox
Subject: Re: cannot send email to hotmail msn issue- SRX060105608293

Dear Shawn,

Do you mean the problem is our DNS server? So far we use our ISP XO DNS( and Even I changed to SBC DNS(, still cannot send to all hotmail email account sucessfully. Do I need contact XO company to ask them check their DNS or what should I do anything else?

Thank you very much,
Have a nice weekend,

----- Original Message -----

From: GEST HM Inbox
To: Support
Cc: GEST HM Inbox
Sent: Friday, January 06, 2006 1:55 PM
Subject: RE: cannot send email to hotmail msn issue- SRX060105608293


Hotmail maintains four IP addresses for each of its four MX sites.  Of the sixteen IP’s, four are rotated offline for maintenance and upgrades.  This shouldn’t pose a problem as long as inbound MTA’s update their DNS and round-robin their attempts to reach

The current MX/IP rotation is as follows: A IN 3600 A IN 3600 A IN 3600
* A IN 3600 A IN 3600
* A IN 3600 A IN 3600 A IN 3600 A IN 3600
* A IN 3600 A IN 3600 A IN 3600

* A IN 3600 A IN 3600 A IN 3600 A IN 3600

*offline for routine maintenance

Note in the log below that your server happens to be pinging only the IP’s that are currently offline.  Try pointing to one or several of the online IP’s and advise us the results.

Thank you,

I really appreciate if can get any help from yours. Thanks again,

fortalkAuthor Commented:
Anyone can help me here?
Hi read my descrition to see if you can resolve the problem. If not, try this web site:

So, it is a good time to summarise the diagnosis procedure so the same problem can be tackled quickly.

It is based on W2k3 , Exchange Server 2k3 environment.
1.)      Check the port of your firewall or setup the NAT in your router if you can not get any mail sent out/got in.
2.)      If only some special domain having problem, then need to look at your DNS. Use nslookup, (u can start it from DNS management console or type in DOS command mode.). the first line will tell you which DNS you are using, if no DNS display, you need to specify a valid DNS on your machine. Then type in the problematic mail DN, e.g. It will show you all the IPs that the DNS can resolve. If no valid IP shown, you need a qualified or updated DNS , I recommended one I hope others can contribute more so we can balance the network traffic to a single DNS.
You also can nslookup the mx server to see if their existence,

If you confirm it is a the DNS problem, you need a new DNS either put into the DNS forward IP option or midify the SMTP protocol in the exchange server management as describe:
Exchange system manager->Administrative groups->First Administrative group->Servers-Your Server->Protocols->SMTP->Right Click Default Virtual Server->Properties->Delivery->Press Advanced Button->Press Configure Button near the Configure external DNS servers-> add a new good one and move to top.
Stop/start the smtp server.
3.)      Still having problem,
You must look at the antivirus program. I had the Norton AV 10 installed. Maybe it is the installation order problem or it is an internal bug of NAV. I have to disable the Internet email Auto-protect to get hotmail email to go out. Remember after clicking the tick box in NAV configure page, you also need to press OK button. Otherwise, this won’t effect.
4) Last try is to disable the EDNS. You need to install the support tool form the W2k3 CD and change dir to the drive:/Program Files/Support tools/ and type in:
dnscmd /config /enableednsprobes 0

But I suspect this will cure the program. Only the last option before reinstallation.
That will most of the program of stuck at some special domain(s). If still not working, I bet you need to reinstall. MS exchange is a long term product, should not be that problematic. So, try to find the  
Bradley FoxLAN/WAN Systems AdministratorCommented:
I suggest splitting the points between the 3 responders.
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Windows Server 2003

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