Exchange 2003 > 2010 Migration - Relay needed?

Hi,

I am on the verge of completing my first Exchange 2003 > 2010 upgrade and I'm 99% there...

All that's left now is final testing of ActiveSync from various mobile devices and the actual mailbox moves/old server decommissioning.

I had a bit of a headache with SSL certificates and an Outlook 2007 popup, but that is now resolved.

The only outstanding issue I have is this.................we have a 3rd party CRM/database system which we use for sending mail to clients & other contacts.

At the moment, it is set up using the following config:

sender e-mail address: user@domain.com
reply e-mail address: user@domain.com

Server: 192.168.1.XXX
Port: 25
Username: domain\username
Password: *password*
Authentication Method: AUTO
SSL? (Tick box): NO

I'm trying to get this application to send via Exchange 2010 but haven't had any joy. I've changed the IP address accordingly and swapped the username/password for a user that has a live 'Exchange 2010' mailbox'.

I have tried all different combinations of SSL on/off and authentication methods but I don't seem to be getting anyway.

Please could someone look into this as soon as possible, I want to carry out the migration this weekend but need to ensure that this e-mail sending method is working fine.

Thanks in advance!!

PS. Error log is attached
robsamuel2k8Asked:
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robsamuel2k8Author Commented:
Sorry, here's the attachment
Error-Log.txt
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Victor TarasovHead of the Department of System AdministrationCommented:
SSL must be trusted. Including the organization that issued the certificate.
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FostWareCommented:
I've had issues getting authenticated SMTP to happen from CLI, so I think I ended up creating an anonymous relay (as per http://technet.microsoft.com/en-us/library/bb232021.aspx) but the source IP was limited and I think I skipped the Add-ADPermission step, since Anonymous connections weren't allowed.

You could also try just running the Add-ADPermission step for that user on a new anonymous relay connector.
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AmitIT ArchitectCommented:
Logs says you are unable to relay, configure the relay connector first.
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Adam BrownSr Solutions ArchitectCommented:
You need to configure your Receive Connector to allow anonymous connections from that IP address. Create a new Receive connector in Exchange 2010 (from Server Configuration\Hub Transport), enter the IP address for the remote mail sending server into the IP addresses tab, and select only Anonymous and Exchange Users on the Permission groups tab and TLS,Basic, and Exchange authentication on the Authentication tab.
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Alan HardistyConnect With a Mentor Co-OwnerCommented:
You need to configure a new Receive Connector and also allow it to Relay.  The MS Guide will show you the exact steps to do both and set this up successfully:

http://technet.microsoft.com/en-us/library/bb232021.aspx
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robsamuel2k8Author Commented:
Hi, I moved all of the mailboxes on Saturday and it all went smoothly. I've re-configured our users' mobiles and I'm working on the CRM e-mail access this morning.

I'll give the links above a try now and let you know how I get on.

Thanks for the advice so far, I will provide feedback as I go through the potential solutions.
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robsamuel2k8Author Commented:
Hi, I've set up a 3rd receive connector and it seems to be working, albeit with a 5-20 second delay between clicking send and getting the 'message sent' popup.

I'm also having trouble with POP3. I've configured it right and tested it internally using PowerShell but one application we use that needs POP3 is not connecting.

Thanks for your comments, I'll do some research on here to figure out the other issues.

Many thanks!
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