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TLS Connect failed....I'm not going to try again

Posted on 2008-10-06
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Last Modified: 2013-11-16
Hi,

I'm having a strange email issue.  Basically, my company can receive most external emails just fine, but
when emails are sent from one particular external domain, the emails get bounced back to the sender SLOOOWLY.
After several days, the sender will receive an email that says something like this:

TLS Connect failed.  connected to xyz.ab.de.fg
I'm not going to try again; this message has been in the queue too long.

The same emails are delivered properly to gmail accounts.

the MX records appear to be fine and I notice no other issues in the logs of our
firewall or exchange server (we're using Exchange 2003).

We thought this might be a TLS issue, but we are receiving TLS-encrypted emails from other domains, so I'm not sure that's the issue.

I've seen similar questions on experts-exchange, but without satisfactory resolution.

Any ideas as to what/where to test?
I'm not a sysadmin/exchange expert...it's just a job I inherited, so go easy!

Thanks!
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Question by:pdanese
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8 Comments
 
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Accepted Solution

by:
dpk_wal earned 300 total points
ID: 22657009
Although I am not an expert on exchange; writing this comment as it might help, I think either NDR or reverse DNS lookup can be the cause of the behavior observed.

Thank you.
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Author Comment

by:pdanese
ID: 22658970
Hi, thank you for the response.

I have a few questions, tho...what is NDR?

also, could you elaborate on reverse dns lookup being 'the cause'?

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Author Comment

by:pdanese
ID: 22658997
i just looked up NDR...that seems to be an error when the recipient doesn't exist.

that is not the case here.  the recipients *do* exist and they receive emails from most sources just fine.  but no one in our domain is capable of receiving emails from one specific external domain.

hope that helps clarify the issue.
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LVL 32

Expert Comment

by:dpk_wal
ID: 22660590
If you are using a firewall which does NAT for your email server and the MX record and the public IP of the firewall are different; the firewall normally sends all outbound traffic from the server using the puclic IP instead of MX record; in this case the domain which is doing reverse DNS lookup would not accept the emails from your domain. To overcome this problem we configure 1-1 NAT; and this ensures that all outbound traffic from server goes out with the same IP as the MX record IP.

As you clarified NDR is not the issue. If this is ruled out then I am not sure what else is the issue.

Thank you.
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LVL 12

Assisted Solution

by:RobinHuman
RobinHuman earned 150 total points
ID: 22660765
This sounds like a TLS authentication issue on the recipient's side - I suggest that you contact them and advise them of this issue - could be the trust with them no longer exists.
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Author Closing Comment

by:pdanese
ID: 31503372
suggestions didn't fix the problem but I wanted to distribute points to close the question.

Thanks to both for responding!
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LVL 32

Expert Comment

by:dpk_wal
ID: 22768402
Thank you for the points.
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LVL 12

Expert Comment

by:RobinHuman
ID: 22768794
Thank you
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