gmail delivery status notification delay

some of our users are complaining that sometimes when they send emails to our company mails from, it is not delivering to the company receipiant mail , they are getting an error

From: Mail Delivery Subsystem <>
Date: 18 April 2010 03:19
Subject: Delivery Status Notification (Delay)

This is an automatically generated Delivery Status Notification



Delivery to the following recipient has been delayed:

Message will be retried for 2 more day(s)

Technical details of temporary failure:
Unspecified Error (SENT_MESSAGE): Connection timed out

when we checked our mails server or antispam device, it shows , there is not such mail arrived at our mail server or our antispam device. Where could be the problem, It is not happening to all the mails coming from  few mails only and to few users

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Could be MX records.

Check that they are configured correctly and are pointing to the right destination.

Use --> MX lookup

mishalkAuthor Commented:
i am using a ipswitch mail service. As i said earlier i am getting mails from the gmail users, but sometimes some mails are missing with the above delivery notification
The notification indicates that the sending MTA could not find a destination for mail.

It is most likely an issue with DNS data. Can you read through my article for DNS (Inbound Mail (The MX record) requirements) and make sure the MX records there actually accept mail for your domain ok.

If you have multiple MX records, they will all need to be tested.

The test can be performed using telnet

telnet MXrecord 25
mail from:<yourGmailAccount>
rcpt to:<>
Test email

Don't forget the .

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mishalkAuthor Commented:
when i do the test

Microsoft Telnet> 25

220 (IMail 11.01 78977-1) NT-ESMTP Server X1
530 user must authenticate on this port
mishalkAuthor Commented:
ooh sorry
i will have to test from external, i tried from internal only. I will do it from external
"530 user must authenticate on this port"

That's not a good sign, that indicates to me that the SMTP service does not accept anonymous sessions, or is specifically configured to reject from the domain in some way.

Either way, a failure of that basic test is pretty significant.

I've connected to the location you specify and it looks as if you have SMTP fixup enabled (normally CISCO device in front of a mail server accepting SMTP connections). It is known to cause issues for some people, I would disable it.

You can see fixup is running as on telnet test you get
220 *************************************************



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mishalkAuthor Commented:
thanks for the quick response, from external we have opened the port 587 to the server. Could you try a test with the domain
domain is,

587 is open fine, but mail from gmail will not  go to this port, it will go to port 25.

You need to get this port functioning correctly and accepting anonymous connections.

mishalkAuthor Commented:
but mails are coming from gmail. only few mails from few users are not able to send some of the mails from their gmail account to company account

once it is reaching the gateway of our network then it goes to antispam-then mail server
external---firewall1-firewall2-antispam device- mail server.

from antispam to mail server it is using port 25

You need a structured approach to troubleshoot this issue. Take note of an email that was supposed to arrive but is missing. Ask for the time the email was sent and the sender address.

Note that mail from gmail WILL ALWAYS arrive on port 25 on the very edge of your network.

You say mail from external goes to firewall1? OK, so check on firewall1 logging (if you have it) whether the mail was received here and forwarded on.

Same for firewall2

Same for antispam device

Same for mail server.

Try to see where it fails.

If you do not have the facilities on the firewalls or antispam to check if the mail items were forwarded, then are you able to eliminate them and add one by one until the problem reoccurs?

I suspect it might be at the very edge, as you appear to be using SMTP fixup
220 ******************************
This is known to cause all kinds of strange problems, so can you turn this off?

You will need to wittle the suspects down here, as there is too much complexity. You need to dig into the logs to see if you can track the message.

mishalkAuthor Commented:
i have turned of the esmtp no inspection..and thanks for the detailed description ..thank you for taking your valuable time , i will follow the rest as you mentioned in your comment
Glad I could help,

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