unable to send mails to hotmail.com

[ravirccc]

I am using wingate mail server for sending the outnound mails and everything works fine from outlook but if i send any mail to hotmail.com it says that mail delivery failure. eg mail id: somex@hotmail.com please help me how to fix this error and is ther anything in settings to check out ? please let me know thanks in advance

[Pascal]

What reasons does it give for the mail delivery failure? You might need to turn on debug logging for the SMTP Server to get more information.

Are you using Hotmail from within Outlook / Outlook Express?

[ravirccc]

This is a system generated message - Please do not reply

----------------------------------------------
Permanent delivery failure
----------------------------------------------

Your message has encountered permanent delivery problems to the following recipients:

Somex@hotmail.com


Reason: Failed all retries, giving up


----------------------------------------------
Your original message (in part):
----------------------------------------------

Received: From SIRI (unverified [192.168.0.104]) by SMTP Server [192.168.0.101] (WinGate SMTP Receiver v6.0.3 (Build 1005)) with SMTP id <0000000547@NODE3>; Mon, 22 Nov 2004 16:40:47 -0600
From: "Ravi " <ravi.r@xxxxx.com>
To: "Somex" <Somex@hotmail.com>
Subject: RE: Thanks for information Frank
Date: Tue, 23 Nov 2004 04:10:41 +0530
Message-ID: <003601c4d0e4$50616ea0$6800a8c0@SIRI>
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_0037_01C4D112.6A19AAA0"
X-Priority: 3 (Normal)
X-MSMail-Priority: Normal
X-Mailer: Microsoft Outlook, Build 10.0.2616
Importance: Normal
X-MimeOLE: Produced By Microsoft MimeOLE V6.00.2800.1441
In-Reply-To: <BAY15-F20RGryWtIIZS00014daa@hotmail.com>

This is a multi-part message in MIME format.

------=_NextPart_000_0037_01C4D112.6A19AAA0
Content-Type: text/plain;
charset="us-ascii"
Content-Transfer-Encoding: 7bit


___________________________________________
I just changes the name of mail ids

[Pascal]

"Reason: Failed all retries, giving up" gives us WinGate's reason for stopping the retry mechanism and is the message delivered to the user.

However, that does not give us any indication of why sending to that domain failed. You should be able to find that in your SMTP log file. (<wingate>\Logs\SMTP Server\SMTP Server.log).

There might be other files that contain more information (Historical). That will show a list of commands executed and what reasons there were for the failures.

[ravirccc]

11/24/04 10:44:56 127.0.0.2 <system> 0000001838 Debug: ==== Server mail3.rediffmail.com closed connection
11/24/04 10:44:58 127.0.0.2 <system> 0000001838 Traffic 21906 186 0 0 13s
11/24/04 10:45:00 127.0.0.2 <system> 0000001841 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:45:00 127.0.0.2 <system> 0000001841 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:45:21 127.0.0.2 <system> 0000001841 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:45:23 127.0.0.2 <system> 0000001841 Traffic 0 0 0 0 23s
11/24/04 10:45:30 127.0.0.2 <system> 0000001850 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:45:30 127.0.0.2 <system> 0000001850 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:45:51 127.0.0.2 <system> 0000001850 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:45:53 127.0.0.2 <system> 0000001850 Traffic 0 0 0 0 23s
11/24/04 10:46:00 127.0.0.2 <system> 0000001856 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:46:00 127.0.0.2 <system> 0000001856 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:46:21 127.0.0.2 <system> 0000001856 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:46:23 127.0.0.2 <system> 0000001856 Traffic 0 0 0 0 23s
11/24/04 10:46:32 127.0.0.2 <system> 0000001863 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:46:32 127.0.0.2 <system> 0000001863 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:46:53 127.0.0.2 <system> 0000001863 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:46:55 127.0.0.2 <system> 0000001863 Traffic 0 0 0 0 25s
11/24/04 10:47:00 127.0.0.2 <system> 0000001869 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:47:00 127.0.0.2 <system> 0000001869 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:47:21 127.0.0.2 <system> 0000001869 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:47:23 127.0.0.2 <system> 0000001869 Traffic 0 0 0 0 23s
11/24/04 10:47:30 127.0.0.2 <system> 0000001875 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:47:30 127.0.0.2 <system> 0000001875 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:47:51 127.0.0.2 <system> 0000001875 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:47:53 127.0.0.2 <system> 0000001875 Traffic 0 0 0 0 23s
11/24/04 10:48:02 127.0.0.2 <system> 0000001886 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:48:02 127.0.0.2 <system> 0000001886 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:48:23 127.0.0.2 <system> 0000001886 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:48:25 127.0.0.2 <system> 0000001886 Traffic 0 0 0 0 25s
11/24/04 10:48:35 127.0.0.2 <system> 0000001895 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:48:35 127.0.0.2 <system> 0000001895 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:48:56 127.0.0.2 <system> 0000001895 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:48:58 127.0.0.2 <system> 0000001895 Traffic 0 0 0 0 28s
11/24/04 10:49:00 127.0.0.2 <system> 0000001900 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:49:00 127.0.0.2 <system> 0000001900 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:49:21 127.0.0.2 <system> 0000001900 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:49:23 127.0.0.2 <system> 0000001900 Traffic 0 0 0 0 23s
11/24/04 10:49:30 127.0.0.2 <system> 0000001907 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:49:30 127.0.0.2 <system> 0000001907 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:49:51 127.0.0.2 <system> 0000001907 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:49:53 127.0.0.2 <system> 0000001907 Traffic 0 0 0 0 23s
11/24/04 10:50:00 127.0.0.2 <system> 0000001914 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:50:00 127.0.0.2 <system> 0000001914 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:50:20 127.0.0.2 <system> 0000001914 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:50:22 127.0.0.2 <system> 0000001914 Traffic 0 0 0 0 22s
11/24/04 10:50:30 127.0.0.2 <system> 0000001922 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:50:30 127.0.0.2 <system> 0000001922 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:50:51 127.0.0.2 <system> 0000001922 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:50:53 127.0.0.2 <system> 0000001922 Traffic 0 0 0 0 23s
11/24/04 10:51:00 127.0.0.2 <system> 0000001931 Requested: SMTP Delivery to hotmail.com [try 20] : Failed to deliver after 20 tries
11/24/04 10:51:00 127.0.0.2 <system> 0000001931 Debug: ==== job completed error 4 with RCP file remaining 0000000689
11/24/04 10:51:00 127.0.0.2 <system> 0000001931 Requested: Returned undeliverable mail for hotmail.com
11/24/04 10:51:02 127.0.0.2 <system> 0000001931 Traffic 0 0 0 0 2s
11/24/04 10:51:14 127.0.0.2 <system> 0000001935 Debug: Delivery for domain cccinc-us.com - MX lookup succeeded
11/24/04 10:51:14 127.0.0.2 <system> 0000001935 Debug: ==== Attempting connection to mail.cccinc-us.com[207.218.241.127]
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 220 virt-207-218-241-125.ev1servers.net ESMTP Sendmail 8.9.3/8.9.3; Wed, 24 Nov 2004 10:51:15 -0600
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: EHLO NODE3
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-virt-207-218-241-125.ev1servers.net Hello ras-KK-116.224.95.61.touchtelindia.net [61.95.224.116] (may be forged), pleased to meet you
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-8BITMIME
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-SIZE 10485760
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-DSN
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-ONEX
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250-XUSR
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250 HELP
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: MAIL FROM:<> SIZE=2675
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250 <>... Sender ok
11/24/04 10:51:16 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: RCPT TO:<ravi.r@cccinc-us.com>
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250 <ravi.r@cccinc-us.com>... Recipient ok
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: DATA
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 354 Please start mail input.
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250 Mail queued for delivery.
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: RSET
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com <=S: 250 Reset state
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: mail.cccinc-us.com C=>: QUIT
11/24/04 10:51:17 127.0.0.2 <system> 0000001935 Debug: ==== Server mail.cccinc-us.com closed connection
11/24/04 10:51:19 127.0.0.2 <system> 0000001935 Traffic 2761 455 0 0 5s

[ravirccc]

This was the SMTP server debug log file data. Can you please let me know why couldnt i am able to send and how can i send? if i send a mail from my yahoo mail id its working but couldnt able to send from outlook

[Pascal]

1/24/04 10:50:30 127.0.0.2 <system> 0000001922 Debug: Delivery for domain hotmail.com - MX lookup succeeded
11/24/04 10:50:30 127.0.0.2 <system> 0000001922 Debug: ==== Attempting connection to mx2.hotmail.com[65.54.190.50]
11/24/04 10:50:51 127.0.0.2 <system> 0000001922 Debug: ==== Server mx2.hotmail.com closed connection
11/24/04 10:50:53 127.0.0.2 <system> 0000001922 Traffic 0 0 0 0 23s

About the only strange thing is that once connected to the server it does not respond. Then, 21 -> 22 seconds later it closes the connection. That looks like a basic timeout.

Are you sure you have everything correctly configured on the Outlook side?

[neil]

This seems to be related to hotmails configuration. If you do an mx lookup for hotmail.com it returns 4 different DNS records, each with 4 different IP's. There's nothing wrong with that. In this case mx2.hotmail.com relates to:

mx2.hotmail.com internet address = 65.54.190.7
mx2.hotmail.com internet address = 65.54.190.50
mx2.hotmail.com internet address = 65.54.252.230
mx2.hotmail.com internet address = 65.54.166.230

these 4 IP's. However connections only seem possible to the latter 2 (ending in .230). The first 2 (ending in .7 and .50) wont accept connections. I tried telneting to these two servers, and both times the connections timed out.

When WinGate on your machine does a lookup for hotmail.com, unfortunatley, by chance it is ending up with the .50 IP (probably because it has been cached somewhere in the chain, either by WinGate's DNS resolver or by your ISP's).

You can flush the WinGate DNS cache, either by clicking the Empty button in the DNS Resolver properties, or by restarting the engine. However if the problem is upstream, or it was WinGate and you wish to make sure WinGate doesn't recieve this IP for hotmail.com again, you should create an entry in your hosts file in %systemdir%\drivers\etc\ for hotmail.com and use one of the IP's that you can connect to. You can check which IP's you can connect to by using telnet and then issuing the command (for example):

open 65.54.166.230 25

if this works, then use this IP for hotmail.com in your hosts file.

Regards

Neil