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

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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harryhelp
Asked:
harryhelp
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1 Solution
 
harryhelpAuthor Commented:
Pls. note that Source Server just says the server's name. I will attach below:
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harryhelpAuthor Commented:
Sorry - here it is:
send4.jpg
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petarlCommented:
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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harryhelpAuthor Commented:
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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petarlCommented:
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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harryhelpAuthor Commented:
Will look into this tomorrow.
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harryhelpAuthor Commented:
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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harryhelpAuthor Commented:
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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petarlCommented:
Can you telnet to that server on port 25 from your exchange server?
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harryhelpAuthor Commented:
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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Jamie McKillopIT ManagerCommented:
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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harryhelpAuthor Commented:
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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Jamie McKillopIT ManagerCommented:
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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harryhelpAuthor Commented:
Any you know that work - both were Google's, so they may not accept Telnet (I assume)....
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Jamie McKillopIT ManagerCommented:
What worked?

JJ
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harryhelpAuthor Commented:
Tried Google and Hotmail, both unsuccessfully. This was both on my server and 7 pc.
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Jamie McKillopIT ManagerCommented:
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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harryhelpAuthor Commented:
Home based DSL - will speak with them.
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Jamie McKillopIT ManagerCommented:
Most ISPs block port 25 on their home-based services to prevent botnets from sending spam.

JJ
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harryhelpAuthor Commented:
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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harryhelpAuthor Commented:
Thank you so much - all working :)

Will open another question for the other questions :)
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