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No Outgoing Mail in Exchange 2010 and OWA issue, and AD integration...

Posted on 2010-08-30
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Last Modified: 2012-05-10
I am a total newbie to Exchange, and am sending it up on a 'sandbox' server. I have set up both mydomain.local and mydomain.co.uk, and have the following three questions:
1) I am unable to send e-mails out, but I can get incoming. I created a send connector (with no difference), please see screenshots below.
2) I keep getting a certificate error when visiting via. HTTPS/443 - do I need to buy a certificate, or is there a workaround?
3) I have seen a setup before that people can add mailboxes from AD - how is this possible?

I know this is a lot of questions - let's hope we get to a solution :)

Thanks in advance !
send1.jpg
send2.jpg
send3.jpg
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Question by:harryhelp
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22 Comments
 
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Author Comment

by:harryhelp
ID: 33562291
Pls. note that Source Server just says the server's name. I will attach below:
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Author Comment

by:harryhelp
ID: 33562295
Sorry - here it is:
send4.jpg
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Expert Comment

by:petarl
ID: 33562403
Do you have any mail filtering server on your network? If you do, then you need to select "Route mail through the following smart host" on Network tab and type in address of that server (IP or name).
If you don't use any mail filters than I suppose your Exchange server is visible from the Internet, which I would not recommend, and then you need to check your firewall settings.

Also, here's a couple of links for external testing of your mail server:
http://www.mxtoolbox.com/diagnostic.aspx
http://www.dnsqueries.com/en/smtp_test_check.php
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Author Comment

by:harryhelp
ID: 33562479
Thanks for your quick reply, petarl.

Except for the Netgear router that it is behind (and ports 25,587,443,80, etc forwarding to it), it is on a completely different network from any other server, so I don't have any other servers on the network.

On the two diagnostics:
MXToolbox - Two warnings, and errors on transcript (I assume because not using one of the accepted domains):
- 5.788 seconds - Warning on Transaction time
-  Warning - Reverse DNS does not match SMTP Banner

Transcript:
HELO please-read-policy.mxtoolbox.com
250 myserver.mydomain.local Hello [1.1.1.1] [140 ms]
MAIL FROM: <supertool@mxtoolbox.com>
250 2.1.0 Sender OK [125 ms]
RCPT TO: <test@example.com>
550 5.7.1 Unable to relay [5132 ms]
QUIT
221 2.0.0 Service closing transmission channel [125 ms]


==========
DNSQueries - All green, except:
The SMTP server does not accept mails to postmaster@[IP_ADDRESS]. This is a very bad thing, as this address is used by people that don't know your domain name! The reported error is:
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Expert Comment

by:petarl
ID: 33562705
It look like your server is reachable from the internet, which is good :). Next thing I would check is server logs - on the following link there are instructions how to turn on SMTP logging - http://exchangepedia.com/2007/05/exchange-server-2007-logging-smtp-protocol-activity.html.

Here are instructions on how to search Message Tracking Log - http://technet.microsoft.com/en-us/library/bb124926%28EXCHG.80%29.aspx - I'd recommend you to go to section " Searching the Message Tracking Logs by Using the Exchange Management Console", it's easier to find message logs that way.

Also, look at the routing logs (when you open toolbox, you'll see link for that) for any errors.
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by:harryhelp
ID: 33563037
Will look into this tomorrow.
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by:harryhelp
ID: 33564825
In case this has any significance, when installing Exchange yesterday (had to wipe server due to AD & domain issues) it didn't install most of the roles. Don't remember exactly what I did, but I managed to install the other roles.

I don't know what the Routing Log is meant to say - but it all looks normal (to my limited knowledge !)

I have enabled SMTP logging, however it only seems to log SmtpReceive - which leaves me thinking that there is something in the way preventing it from reaching the Send Connector - any ideas ??
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Author Comment

by:harryhelp
ID: 33564853
Aah, it's now generated a log - but it doesn't look to healthy:


#Software: Microsoft Exchange Server
#Version: 14.0.0.0
#Log-type: SMTP Send Protocol Log
#Date: 2010-08-31T07:25:46.314Z
#Fields: date-time,connector-id,session-id,sequence-number,local-endpoint,remote-endpoint,event,data,context
2010-08-31T07:25:46.314Z,For Internet,08CD16EE3BE37DCF,0,,74.125.39.27:25,*,,attempting to connect
2010-08-31T07:25:46.314Z,For Internet,08CD16EE3BE37DCE,0,,74.125.39.27:25,*,,attempting to connect
2010-08-31T07:26:07.343Z,For Internet,08CD16EE3BE37DCE,1,,74.125.39.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.39.27:25"
2010-08-31T07:26:07.343Z,For Internet,08CD16EE3BE37DD0,0,,74.125.53.27:25,*,,attempting to connect
2010-08-31T07:26:07.343Z,For Internet,08CD16EE3BE37DCF,1,,74.125.39.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.39.27:25"
2010-08-31T07:26:07.343Z,For Internet,08CD16EE3BE37DD1,0,,74.125.155.27:25,*,,attempting to connect
2010-08-31T07:26:28.372Z,For Internet,08CD16EE3BE37DD0,1,,74.125.53.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.53.27:25"
2010-08-31T07:26:28.372Z,For Internet,08CD16EE3BE37DD2,0,,74.125.95.27:25,*,,attempting to connect
2010-08-31T07:26:28.372Z,For Internet,08CD16EE3BE37DD1,1,,74.125.155.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.155.27:25"
2010-08-31T07:26:28.372Z,For Internet,08CD16EE3BE37DD3,0,,74.125.95.27:25,*,,attempting to connect
2010-08-31T07:26:49.401Z,For Internet,08CD16EE3BE37DD2,1,,74.125.95.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.95.27:25"
2010-08-31T07:26:49.416Z,For Internet,08CD16EE3BE37DD4,0,,74.125.65.27:25,*,,attempting to connect
2010-08-31T07:26:49.416Z,For Internet,08CD16EE3BE37DD3,1,,74.125.95.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.95.27:25"
2010-08-31T07:26:49.416Z,For Internet,08CD16EE3BE37DD5,0,,74.125.43.27:25,*,,attempting to connect
2010-08-31T07:27:10.445Z,For Internet,08CD16EE3BE37DD5,1,,74.125.43.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.43.27:25"
2010-08-31T07:27:10.445Z,For Internet,08CD16EE3BE37DD6,0,,72.14.213.27:25,*,,attempting to connect
2010-08-31T07:27:10.445Z,For Internet,08CD16EE3BE37DD4,1,,74.125.65.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.65.27:25"
2010-08-31T07:27:10.445Z,For Internet,08CD16EE3BE37DD7,0,,74.125.91.27:25,*,,attempting to connect
2010-08-31T07:27:31.458Z,For Internet,08CD16EE3BE37DD6,1,,72.14.213.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 72.14.213.27:25"
2010-08-31T07:27:31.474Z,For Internet,08CD16EE3BE37DD7,1,,74.125.91.27:25,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 74.125.91.27:25"
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Expert Comment

by:petarl
ID: 33585555
Can you telnet to that server on port 25 from your exchange server?
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Author Comment

by:harryhelp
ID: 33585593
Failed:

C:\Users\Administrator.MYSERVER>telnet 74.125.91.27 25
Connecting To 74.125.91.27...Could not open connection to the host, on port 25:
Connect failed
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 33588979
Hello,

If you can't telnet to that IP there is something blocking the connection at the network level. Is the firewall turned on on your Exchange server? Is the netgear router configured to block any outbound ports?

JJ
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Author Comment

by:harryhelp
ID: 33589065
Good point, but no outbound ports set to block on the router (actually set a special rule to allow TCP port 25, just in case!), and same problem even when firewall is off.

Thanks for your reply, by the way :)
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Expert Comment

by:Jamie McKillop
ID: 33589126
Can you try the telnet command from another system on your network? Can you try to telnet to a different external mail server?

JJ
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Author Comment

by:harryhelp
ID: 33589137
Any you know that work - both were Google's, so they may not accept Telnet (I assume)....
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Expert Comment

by:Jamie McKillop
ID: 33589241
What worked?

JJ
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Author Comment

by:harryhelp
ID: 33589275
Tried Google and Hotmail, both unsuccessfully. This was both on my server and 7 pc.
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 33589325
What type of internet line do you have? Do you have a dedicated business line or are you on a home based line, like DSL? Depending on your service, your ISP may be blocking outbound port 25.

JJ
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Author Comment

by:harryhelp
ID: 33589364
Home based DSL - will speak with them.
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Accepted Solution

by:
Jamie McKillop earned 500 total points
ID: 33589388
Most ISPs block port 25 on their home-based services to prevent botnets from sending spam.

JJ
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Author Comment

by:harryhelp
ID: 33589476
Yep, you're right!

They do have a mail relay though, so will configure Exchange to use that and report back.
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by:harryhelp
ID: 33589545
Thank you so much - all working :)

Will open another question for the other questions :)
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