Exchange 2010 SMTP outbound connector not flowing

I have a SBS 2011/ Exchange 2010 set up. Incoming mail from the hosted domain (xxxx.edu) is fine. I used the wizards for the inernet connection and internet mail, etc. It set up the SMTP send connector just fine. FixMyNetwork says there are no errors with the network.

On the Windows SBS connector properties I have FQDN as remote.xxxx.edu, Address Space is  "smtp   *"  scoped box unchecked,    Network is Use DNS, Enable DNS security unchecked, No smart host, Use External DNS of transport box unchecked,   Sourceserver is the server.

All the normal stuff the wizard sets up for you.  When I connect to exchange from an Outlook 2010 client I can receive emai, but no email goes out. It leaves the Outbox but never shows up at the destination.

What could be causing the SMTP connector to not send the mail?    THANKS!
dgrendaAsked:
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Alan HardistyCo-OwnerCommented:
Default port is port 25.  It could be the Router not allowing TCP port 25 outbound from the server (if you can't telnet to me on IP / FQDN on port 25 - something is blocking you - the fact it fails on both shows it is not a DNS issue).

If you use another port - you will have to use a smarthost and that will have to be your ISP's smarhost (mail server) and the port will be what they tell you to use.

Alternatively you need a 3rd party filtering service and their Smarthost / port combination.
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Alan HardistyCo-OwnerCommented:
Are you able to telnet from a command prompt to my mail server on port 25?

telnet mail.mydomain.co.uk 25

or

telnet 188.220.xxx.xxx 25

Please try both and post the results.

Alan
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Hypercat (Deb)Commented:
In additionl to using the telnet test mentioned by alandhardisty, have you checked the emails queues on your SBS server? The Queue Viewer can be opened by opening the Exchange Management Console, clicking on Tools and then Queue Viewer. When you look at the Queue Viewer, do you see the mail building up in the queues? What queue is showing the buildup? What error messages are being shown there, if any?
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dgrendaAuthor Commented:
Tried both telnet and both failed. Unable to open connection.

Trying Queue thing now.
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dgrendaAuthor Commented:
They are stacked up in the Queue:  SCL is -1 and it sayd message delayed  Error 400.4.4.7  (excuse the security xxxx)

Identity: XXXXSERVER\12\60
Subject: test 5
Internet Message ID: <AAC786AFAC112F43BCA8F09F54DFADF7022602F1@xxxxSERVER.XXXXinst.local>
From Address: dgxxxa@xxxxinst.edu
Status: Ready
Size (KB): 4
Message Source Name: FromLocal
Source IP: 255.255.255.255
SCL: -1
Date Received: 2/23/2011 10:02:22 AM
Expiration Time: 2/25/2011 10:02:22 AM
Last Error: 400 4.4.7 Message delayed
Queue ID: xxxxSERVER\12
Recipients:  david@xxxa.com
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Alan HardistyCo-OwnerCommented:
Okay - if both failed, your ISP or your firewall is blocking TCP port 25 outbound.

Check the firewall / router first please, then get on the phone and give your ISP a hard time until they unblock you!!
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dgrendaAuthor Commented:
So you are saying it could be the Linksys router?  And is there another port option or am I stuck with 25?

Can I change that somewhere in Exchange?  THANKS!!!!
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dgrendaAuthor Commented:
Looks like it's port 25 and thanks for the tip on the queue check
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dgrendaAuthor Commented:
Is there any way to change Exchange to use port 587 instead?
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Alan HardistyCo-OwnerCommented:
Yes - use the following command in the Exchange Management Shell:

Set-SendConnector -Identity "Send Connector Name" -port 587

Change the Send Connector Name to match your Send Connector
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Alan HardistyCo-OwnerCommented:
You will have to send mail to a smarthost if you change the default port so you will need to modify the default Send Connector accordingly.
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dgrendaAuthor Commented:
Smarthost like my ISP's SMTP server?

I use port 587 on my stand alone outlook 2003 outgoing. I have to say it requires authentication, same as incoming.

Sorry if I seem so unclear
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Alan HardistyCo-OwnerCommented:
No problems - it's a complicated beast Exchange!

Yes - a Smarthost is your ISP's SMTP server - if you change the port you will have to send ALL mail to a Smarthost for delivery.

Have you spoken to your ISP and asked them if they are blocking port 25?  Sometimes they will say No even when they are.  Tell them you can prove they are blocking you and then talk to someone in 2nd line / 3rd line support until you get some joy.

Using port 25 means you can send all mail out via DNS which is the normal method.
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dgrendaAuthor Commented:
I am actually configuring an exchange server to be installed eventually in a business location. So I'm hesitent to jump thru too many hoops to get it working in my home office.  I am surprised Exchange doesn't just allow you to change ports like Outlook and be happy.

I also have to get stupid BBerry Enterprise Express working on this beast.

Ah I understand the port 25 DNS relatiosnhip. Ok that makes sense. YOU sir, are a steely eyed missle man.

Thank you. You have helped me before.
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Alan HardistyCo-OwnerCommented:
: ) - Not been called that before!!

If you are on a home DSL service (Dynamic IP Address), chances are that Port 25 is blocked as standard.

Sounds like the server is configured happily - it usually works out of the box, so don't tweak it and when you move it - it should be fine.

Good luck with the BB - not a fan personally.
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dgrendaAuthor Commented:
One more question. Will it solve my problem to use a smarthost and not worry about the port? or is the port going to be a problem no matter what.
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dgrendaAuthor Commented:
You answered that. Thanks!

I hate BBerry too.
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