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Messages stuck in Queued state Exchange 2003

Over the past two days, two of our employees have tried sending an email to one of our clients and these emails are sitting in a Queued state and not being delivered.  There are six emails to this client.  Does this mean that our email server is not getting a response from the mail server at the clients domain?  How can I test this or see if this client's email/domain is the problem or tell if the problem is our server?  All other emails are going through just fine it seems, it's just these six emails.  This is one of our bigger clients and my sales guys are not happy their emails aren't being sent and I am not sure what to tell them.

Thanks
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jbobst
Asked:
jbobst
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2 Solutions
 
Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Yes there might be an issue on the client end.

Try tos end an email from external and check. also if the issue is just with one email address or domain pollibly their issue.

- Rancy
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smckeown777Commented:
They are sitting in a queued state - what's the NDR code in the queue?

Open System Manager and drill down into the Queue section, if mails are sitting there'll be a error code relating to why they are queued - post that here so we can help
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jbobstAuthor Commented:
I don't see any errors.  Their status is still Queued, not "non delivered" yet.  I believe they have two days before they expire and get non delivered.  My users received an email from the exchange system just saying it's been delayed - here is the email message they got:

This is an automatically generated Delivery Status Notification.

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.


When I highlight the domain in the "Queues" area in the Exchange System manager, at the bottom there is a message that says "The remote server did not respond to a connection attempt".  Sounds like it's something on their end maybe?  Is there way (besides sending the client an email from my yahoo or gmail account) to test on the public internet the domain name to see if it's working properly?  Some sort of internet tool for mail delivery?
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smckeown777Commented:
Yes, use this site...

www.mxtoolbox.com

Enter their domain and it will test to see if they are responding to emails

Sounds like its a connectivity issue with their side...
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
I believe they have two days before they expire and get non delivered - Absolutely

The remote server did not respond to a connection attempt - Clearly says issue with Recipient Server :(

You can check with their MX record or IP and then try to telnet and see if you can drop an email

- Rancy
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jbobstAuthor Commented:
mxtoolbox.com reports:

10       antispam01.maxim-ic.com       205.153.101.182       24 hrs       Blacklist Check      SMTP Test
10       antispam02.maxim-ic.com       205.153.101.183       24 hrs       Blacklist Check      SMTP Test

Not sure what to make of it.
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smckeown777Commented:
Do the SMTP test to see what it reports...
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
I would also like to check if they arent blacklisted as if so they will have issues with receiving emails as well as other domains in sending emails to them.

If they are blacklisted do let them know so they can work to try and get themselves delisted.

- Rancy
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jbobstAuthor Commented:
SMTP is all good, except for the warning saying it does not support TLS.  Everything looks good on the black list too.
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smckeown777Commented:
Ok, one last thing to test just to make sure - test your own domain on that site - blacklist check, etc...just in case you've been blacklisted somehow

This client you're emailing - has worked previously yes?
The outgoing emails - big attachments? What size are they?
Anything changed on your server in the last few days since it previously worked?
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jbobstAuthor Commented:
I did a black list check for my domain...all looks good except there was a couple time outs.  Did a second and third check and the time outs were gone on the second check then there were time outs for two other black lists but the first two time outs were now ok.

Emails have been sent to this customer for a long, long time sucessfully

The emails have no attachements

Nothing changed on our server that I am aware of  We have a small business with one server and just me trying to manage the IT needs
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Is there a blacklist for the recipient domain ?
Issue is more on the recipient end as only one doamin is affected .... if it would have been your server everything would have been halted.

- Rancy
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jbobstAuthor Commented:
When I check the blacklists for the recipient domain, everything looked good there too.  We contacted the IT people at the recipient's company, and they are looking into it.
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Good let us know .... also were you able to telnet on port 25 to their MX entries ?

- Rancy
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jbobstAuthor Commented:
I don't know how to telnet and haven't tried that.  I'll do some digging see if I can find some instructions on how to do it.
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smckeown777Commented:
telnet <their mail server ip> 25

Will open a prompt and should show their sides Exchange server name...

telnet 1.1.1.1 25 - note the space between ip and 25
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jbobstAuthor Commented:
From my laptop (windows 7) do I type the telnet <server> 25 from the run command, or a command prompt?  Neither of those work.
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jbobstAuthor Commented:
Sorry, just read I need to install it from Windows features.
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smckeown777Commented:
Yep. its not installed on Win7 by default
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
You can do that from your Exchange box as well.
Try with Telnet "IP of recipient server" 25

- Rancy
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jbobstAuthor Commented:
When I did the telnet 205.153.101.182, it returned:

220 antispam.maxim-ic.com ESMTP

Is that what I am looking for and are there any other steps to perform?
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smckeown777Commented:
Well that confirms you can access...next step is to try to send email using that command line...going to see if I can dig out the exact lines you need...or maybe Rancy has those handy
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smckeown777Commented:
Here are steps to test email sending

First, telnet to the REMOTE server, in your case thats...

telnet remoteip 25
and press enter.

helo <your fqdn>

MAIL FROM: whatever@yourdomain - note enter a valid email here(and enter)

rcpt to: remoteuser@remote.com and enter. (valid remote email here)

DATA and enter.

subject: test and enter.

Test message and enter.

Type .
and enter

Quit

All entries in black/bold above are what you type in telnet session
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jbobstAuthor Commented:
Ok, after the helo, I received the "pleased to meet you", so I assume that worked
Then I got an "OK" after I put the mail from email (my email), so I assume that worked
Then on the first rctp to: request, I got an  error 550 No such domain at this location
I typed the exact rctp to: command again, and this time I got and "OK"
Then after the DATA, subject: and test message, I got a 250 Ok: queued as 90AC8191D4C0 response

I then closed the connection.  I find it strange that the first time I put the recipients email address in, it said no such domain, and then it worked ok the second time.  Any idea what that means?
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smckeown777Commented:
Well depends...did you type it EXACTLY correct? Reason is, if you mistype in the telnet session it doesn't like it, it can complain with just one space out of sync!!

Sounds good though, its the normal messages I'd expect from a telnet session...
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
smckeown777: Thanks for sharing the telnet droping email details.
jbobst: This all looks good not sure then what could be the issue with sending email to the user.

- Rancy
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smckeown777Commented:
At the same time maybe there is a config issue on the client end...based on it complaining about the 'no such domain'

Since you've already contacted the client IT people lets see what they say...
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jbobstAuthor Commented:
Update -

I got a reply last evening from the telnet email I sent, so the telnet was successful.  This morning when I got into the office I noticed all the emails were still stuck in the queue on our exchange server.  I did a full reboot on our exchange server, and once that happened all the emails went out successfully.  I have no idea why that is, but I suppose I am glad it's working now.

Thanks for all the help, and I'll close this out this question.
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jbobstAuthor Commented:
The experts helping me were fantastic.  They responded quickly, provided exact details and were very helpful.
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