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I am having some problems with emailing to a couple of specific gmail addresses, but not all gmail addresses. I'm running Exchange 2010. Here is the error:

Diagnostic information for administrators:

Generating server:

Reporting-MTA: dns; EXCH

Final-recipient: X-MAILTO;
Action: failed
Status: 5.4.0

Any suggestions?


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That error looks funny.. have you mangled/rewritten the output? – pauska Sep 20 '12 at 23:02
Full Error: Generating server: # #MAILTO# --002_7880678070687665717270757274697875807175707870777367707 Content-Type: text/html; charset="us-ascii" Content-Transfer-Encoding: quoted-printable --002_7880678070687665717270757274697875807175707870777367707-- --000_7880678070687665717270757274697875807175707870777367707 Content-Type: message/delivery-status Reporting-MTA: dns; EXCH Final-recipient: X-MAILTO; Action: failed Status: 5.4.0 – Joshua Cook Sep 20 '12 at 23:32
I just modified the email address... – Joshua Cook Sep 20 '12 at 23:34

Errors like these are usually problems related to DNS resolution.

Try to run nslookup locally on your exchange server:

set type=mx

Look at the results (run the query several times), and see if stays coherent. Check with an outside client against a different DNS server and see if it matches.

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OK, it seems to stay the same. What do you think my next step should be? Would it help to flush the DNS cache? – Joshua Cook Sep 20 '12 at 23:23
OK, I'm noticing that doing the nslookup from inside is giving me my server name and address, and then the FQDNs of the gmail servers. From outside, I get server and address unknown and the FQDNs of the gmail servers. – Joshua Cook Sep 20 '12 at 23:29
Server address is just the DNS server you're using, so that should be different. I guess you'll just have to dig in your logfiles. – pauska Sep 20 '12 at 23:31
That just means that externally nslookup can't resolve the name from the ip address of the DNS server you're running nslookup against. It's completely normal and doesn't have any bearing on DNS resolution. – joeqwerty Sep 20 '12 at 23:33

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