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IIS SMTP Mail Never Leaves Queue

Posted on 2009-04-03
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Last Modified: 2013-11-30
I have read so many posts about this and none seem to relate to me. I have just setup a new SMTP Virtual Server in IIS, with the Default Local Domain, and a domain I have pointed at an ip on the box for type remote.

When I put a test mail in the pickup directory, the server picks it up and adds it to the queue directory and that is as far as it goes. I see the following in the web log, any ideas on how I can get this to work? What am I missing here?

2009-04-04 01:59:13 209.85.221.44 OutboundConnectionResponse - - 220+mx.google.com+ESMTP+10si2912969qyk.125 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionCommand EHLO - C59409-120719 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionResponse - - 250-mx.google.com+at+your+service,+[74.55.233.130] 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionCommand MAIL - FROM:<XXXXXXXXXXXXXXXX@XXXXXXXXXXXXXXXX.net>+SIZE=357 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionResponse - - 250+2.1.0+OK+10si2912969qyk.125 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionCommand RCPT - TO:<XXXXXXXXXXXXXXXX@gmail.com> 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionResponse - - 250+2.1.5+OK+10si2912969qyk.125 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionCommand DATA - - 0 0
2009-04-04 01:59:13 209.85.221.44 OutboundConnectionResponse - - 354++Go+ahead+10si2912969qyk.125 0 0
2009-04-04 02:09:13 209.85.221.44 OutboundConnectionResponse - - 451+4.4.2+Timeout+-+closing+connection.+10si2912969qyk.125 0 0
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Question by:addicktz
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LVL 25

Assisted Solution

by:Ron Malmstead
Ron Malmstead earned 200 total points
ID: 24065888
Do you have any firewall that might be inspecting the smtp packets ?

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_22069551.html
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LVL 2

Assisted Solution

by:ibiadmin6
ibiadmin6 earned 50 total points
ID: 24072814
Turn off AV scanning of the SMTP directories and see if it works then
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LVL 14

Accepted Solution

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wolfman007 earned 250 total points
ID: 24088509
Have you configured your Virtual SMTP Server to relay your emails to a Smart Host?

If you do not tell the server where to send the emails then they will just sit in the queue.

To set up a smart host
1. In IIS Manager, right-click the SMTP virtual server, and then click Properties.
2. Click the Delivery tab, and click Advanced.
3. In the Smart host box, type the name of the smart host server. You can type a string to represent a name or enter an IP address.
4. If you want the SMTP service to attempt to deliver remote messages directly before forwarding them to the smart host server, select the Attempt direct delivery before sending to smart host check box. The default is to send all remote messages to the smart host, not to attempt direct delivery.
 
from

Configuring Smart Hosts (IIS 6.0)
http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/6003ab51-7eb5-47b2-8d92-e26b1deeeac1.mspx?mfr=true
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LVL 25

Assisted Solution

by:Ron Malmstead
Ron Malmstead earned 200 total points
ID: 24088598
wolfman....why do you assume he needs to use a smarthost ?...

Have you tested sending an email to an address other than a *gmail address ?... From your post above it looks like your server connected to google to try to deliver mail, then timed out...or the connection was closed by google mail server.
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