Exchangeserver 2003 SBS wont send e-mail. I use outbound.mailhop.org

Hi Experts,

Please help. We have an SBS server 2003 std edition.

My quesry is in regards to exchange. Up until yesterday i am unable to send e-mail. I can see in system manager that the queue shows aprox 200 e-mails. The additional info is "The remote server did not respond to a connection attempt"

I had looked over my settings for over an hour and everything looks fine and unchanged. The only thing that happened was when i thought i had exhausted all possibilities i checked if the server was black listed and i found it was blacklisted by baracuda spam on the net. I e-mailed and had this lifted and they confirmed by e-mail that we have been removed.

I can confirm that no other servers have stopped us. My mail still wont go. I have restarted the exchange server services, the entire server and no luck.

I recreated y default SMTP virtual server and still no luck. I do use DYNDNS's outbound mail hop service to send mail via a setting for smart host. I tried the alternative TCP ports and no luck.

I have e-mailed them to see if they have restricted me but no answer yet. I did log into my account and could see nothing informing me i have been blocked.

What should i try next. The only thing i have not tried and has always been a grey area for me is telnet to see if the ports are open. Will this help?

Thank you
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DCHMIELAsked:
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DCHMIELAuthor Commented:
Sorry just to add event viewer shows no faults for this.

thx
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didnthaveanameCommented:
You are using outbound.mailhop.org as a smarthost correct?

If so from the exchange server open a command prompt then type "telnet outbound.mailhop.org 25"

Then once you see the banner for mailhop type the commands below and let us know if your email comes through. (replace your@emailaddress with your actual email address and external@ with an email address that is hosted out side your network)

helo localhost
mail from:you@emailaddress.com
rcpt to:external@someotheraddress.com
data
test
.
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DCHMIELAuthor Commented:
Hi

When i enter the command i get this? I cant proceed any further.


C:\>telnet outbound.mailhop.org 25
Connecting To outbound.mailhop.org...Could not open connection to the host, on p
ort 25: Connect failed

C:\>
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DLeaverCommented:
Try using this MS tool to see where the mail is stopping, it uses the Telnet command in its diagnostics.

Once unpacked navigate to the SMTPDIAG tool via command line and run the following

>smtpdiag.exe youremail@emailaddress.com problemaddress@externalladdress.com /v

http://www.microsoft.com/download/en/details.aspx?id=11393

Post the results here if you want us to decipher anything for you
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DLeaverCommented:
I just posted after you, still worth running the tool

Not trying to jump on didnthaveanames post but this output indicates port 25 to your outbound hop is closed and the SMTP conversation has been ended, you can go no further

Try changing your Smtp connector to use DNS rather than a smarthost and see if your your mail goes, I don't recommend this set up for any perod of time but if the mail starts to go then your smarthost is causing the issue...

I am guessing you have a dynamic IP that you are sending from?
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didnthaveanameCommented:
Your not jumping on my post. :)

Dleaver is right. It looks like you are blocking outbound 25 or the smart host is blocking your IP address.  I can telnet to the address here without issue.
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DLeaverCommented:
Same here, no issue telnetting - I would consult your Smarthost provider, they may have received SPAM email or suspect you are relaying SPAM so they have blocked you.
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DCHMIELAuthor Commented:
HI

Firstly thank you for the support guys,

Ok had trouble getting the tool to run but after a while got it working. All test came back succesfull.

I too believe they are blacking the port. They provide 3 to use 25, 2525 and 10025

I have tried all these and they dont work.

Dyndns is in america and seems like i will have to call to see if they are blocking me. So frustrating as everything seems to be set up correctly.

Is there anything else i must try or must i see what dyndns say.

To answer one of your questions i have a static IP address

Thank you
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DLeaverCommented:
You could use your ISP's smarthost if they provide one, eliminate the need for DynDNS altogether.

However it would be worth, if you havent doen so already, locking down your firewall so only your server is sending out on port 25, and scanning it with your AV just to make sure a bot isn't relaying email and causing your the block list issue
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didnthaveanameCommented:
Also have any firewall changes been made?  

Can you telnet to a yahoo mail server on port 25?  Try the command and see if you get the same message or if it lets you connect:

"telnet mta5.am0.yahoodns.net 25"

If this fails my guess is you are looking at a issue on your end.  If it is successful then you pretty much need to talk with DynDNS (if you want to keep using their service )

I agree 100% with DLeaver if you can block port 25 outbound for everything other then your exchange server then its a good idea.  After all you where probably on a blacklist for a reason :)
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DCHMIELAuthor Commented:
Hi Everyone,

Sorry for the delayed response. I had such a problem dealing with dyndns that it took days to fix. The time difefference between myself and america did not help things.

It was in fact DYNDNS that blocked me from using their services. I called another company locally and managed to get a 30 day trial and it got e-mail sending again. Only late last night DYNDNS unblocked my account.

Thanks for all the help. I did like the SMTP tool and will use that in the future.

Thanks again.
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