outbound.mailhop.org failing

I've been using mailhop.outbound.org, DynDNS's mail relay service for Outbound mail through Exchange.    I've got two domains that I send mail from through Exchange.    Lately my outbound traffice to companies like generac.com and adobe.com can sit in my queue and are not relayed through the mail relay service.    My clients get messages back that say:

joe(not his real name)@adobe.com on 4/10/2010 11:01 AM
            Could not deliver the message in the time limit specified.  Please retry or contact your administrator.
            <myexchangedomain.com #4.4.7>


Dyndns tells me that they're not having any trouble with the mailhop.outbound.org service.  

I'm looking to try to indentify the problem and resolve the issue.

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kdubendorfAsked:
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shauncroucherCommented:
Can you telnet to their service successfully?

Can you send any email from your system?

do you always have problems with the domains in question or it is intermittant?

Shaun
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kdubendorfAuthor Commented:
It looks like I can telnet successfully.  I get a message that mentions that it is forbidden to use this system for unsolicited electronic mail.

I can send email from this system to most everyone else

The problems with these domains seem to have started within the last 2 weeks.
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shauncroucherCommented:
What happens if you try sending a message to these domains using telnet?

So, connect to the server and immitate the email message:

http://support.microsoft.com/kb/153119

Shaun
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kdubendorfAuthor Commented:
Shaun,

I'm using mailhop.   Everything I send goes through their service.   Are you suggesting that I telnet to them?

Karl
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shauncroucherCommented:
Yes, to see if their servers accept the mail from a telnet session from you.

If telnet fails, I'd be back to the provider for explanation. If it goes through, I'd be looking closely at DNS settings and Exchange as next troubleshooting steps.

Be careful with telnet commands, because one typo and you have to start again which is irritating (no backspace).

Shaun
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kdubendorfAuthor Commented:
Not sure what the problem is at this point.   Many messages are going through the mailhop portal.   There are a group of messages stuck in the queue that I can't move.    Once the senders were deleted and recreated the new mail is routing properly.   I'll try to type more about this once I see what happens when the messages age out of the queue.
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shauncroucherCommented:
Did you run the telnet test?

Shaun
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kdubendorfAuthor Commented:
Yes I ran the telnet test and was able to connect fine.  I'm finding that all of my test messages are goinng through.   So are most everyone else's mail.   I have two people who seem to be sending mail to certain users that stay in the queue.   They both are connecting via Outlook over http.   My security certificate is good.    I can also send mails to their addressees from the administrator account with OWA without any trouble.   There are two domain names that we use for sending mail from this server.   The people with the problems are the ones using the secondary domain.
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shauncroucherCommented:
What version of Exchange are you using?

What is the error message in the queues for these mails?

Do you have an SPF setup for the secondary domain, does it include you mail server?

nslookup -q=txt seconddomain.com

If you try to telnet test to the mailhop server using the secondary domain,
ie: mail from:<email@secondarydomain.com>

does it work?

Shaun
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kdubendorfAuthor Commented:
Telnet works.

SPF maybe an issue.

nslookup -q=txt secondomain.com (first too)  yields:
C:\Documents and Settings\Administrator>nslookup -q=txt numer
Server:  server.domain.local
Address:  192.168.16.4

*** No text (TXT) records available for seconddomain.com

I get the same for firstdomain.com too.
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shauncroucherCommented:
What version of Exchange are you using?

What is the error message in the queues for these mails?

Shaun
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kdubendorfAuthor Commented:
One other issue.  I do have a reverse dns setup but only for firstdomain.com.   Since I'm using mailhop I don't believe that comes into play.
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shauncroucherCommented:
thats right, as you are using a smarthost, you dont need to worry about rdns.

shaun
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kdubendorfAuthor Commented:
I'm running Exchange 2003 in SBS 2003.   The only error message that I'm getting in the queue is unable to open message for delivery.
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maytrixCommented:
Are you on Verizon FIOS by any chance?  They recently started blocking port 25 outbound.  Just set the send connector to use 2525 - that is another port supported by mailhop.

The commandlet to do this is -

Set-SendConnector -Identity "SENDCONNECTORNAME" -port 2525
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skypilott2Commented:
maytrix, thanks so much for your answer.

I have been looking for an answer to my 'queue' problem for 2 days, and stumbled upon your answer. Since I have Verizon FIOS, as soon as I set the send connector to port 2525 --- voila!

My queue was flushed...fabulous!!!

skypilott2
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kdubendorfAuthor Commented:
I never found an answer for this issue.  It is no longer a problem.  I'm awarding points to shauncroucher.
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