Using Exchange 2007, fully patched as of last month's patches.
Server 2008 SP2, current as Exchange.
No Edge server, Exchange is a standalone.
Server is NOT a domain controller.

We have been having a problem the last couple of weeks with our Exchange
2007 server and sending mail. There are some domains where the mail will
not  be sent. Other domains are just fine. I have done the RBL thing via
MXToolbox, and we are not listed on any of the lists they cover. Checked for
any solutions to possible grey listing, and come up with no answers there
other than that Exchange can handle it. Black hole routers seemed a
possibility, but if the server is restarted, all mail in the queues goes
out, which pretty much rules out an MTU problem. DNS problems were
suggested, but I do not think that is a problem as mail goes out after a
restart, the internal DNS is located on another server, The initial
connection with the SMTP servers receiving mail is successful, and pinging
here, there, everywhere by name returns an IP and usually returns a
successful result for the ping.

Near as I can determine, this is the end of the failed transactions:
MAIL FROM:<st...@mydomain.com> SIZE=20007,
RCPT TO:<u...@verizon.net>,
250 2.5.0 Address and options OK.,
421 4.4.2 Timeout while waiting for command.,
QUIT,

Using TELNET to send to the problem domains is a crap shoot. Sometimes it
works, other times it times out as above.

Remember, this only happens with some domains, not all. I can send to AOL,
but not Verizon.net. I can send to Gmail, but not to the domain of one of
our customers. A restart of the server, not a restart of services, will
resolve the issue for a period of time, but not more than a few hours. This
is hard to tell, since we never know what domains we will have problems
with, though Verizon (who is also our Internet and phone provider, seems to
be a constant).

-- 
\\Steve//

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