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SQL Monitor 2.3.0.334 Email Issue With Exchange 2010

So I finally got around to upgrading from 2.2.0.260 to 2.3.0.334 on one of my two SQL Monitor servers. Everything went smoothly during the upgrade, however, we recently upgraded our Exchange server from 2003 to 2010 and when I try to use the new email server I get "Unable to send test email. Please check your settings." If I switch it back to the 2003 server, it works fine. I asked our IT Admin to look at the logs on the Exchange server, and he said it looks like it's trying to authenticate using the machine account. As a test, I put in my domain credentials and it works against the new Exchange server. The odd thing is that my other SQL Monitor box (v 2.2.0.260) works without using authentication on the new Exchange 2010 server.

Has anyone else had this problem using Exchange 2010 without using an account (Mail server requires a user name and password), on version 2.3.0.334.

Other pertinent information: 
Web Server
Version:	2.3.0.334
Web Server:	Mono.WebServer2/0.2.0.0
Server Name:	http://My-ServerName:8080
Server HOST .NET:	.NET 3.5 SP 1
Server Path:	C:\Program Files\Red Gate\SQL Monitor 2\Web\WEBSITE
Hosted Environment:	32Bit
User:	NT AUTHORITY\NETWORK SERVICE

Base Monitor
Version:	2.3.0.334
Base Monitor:	localhost:7399
Install Location:	C:\Program Files\Red Gate\SQL Monitor 2\BaseMonitor
Host Environment:	32Bit
User:	 DOMAIN\Service.Account
Domain:	DOMAIN
Database:	DB-Server *** RedGateMonitor_DEV
linque
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  • Brian Donahue
    I believe we are working with you on this via email but SQL Monitor can only use SMTP authentication so it probably doesn't work with Exchange 2010 out of the box.

    You'd have to allow the monitor server to connect SMTP by address, then configure Exchange to allow SMTP authentication. Because this mechanism is insecure (the username is plaintext and the password is easily reversible) you may want to enable TLS encryption. Then configure SQL Monitor with a username and password and enable TLS.
    Brian Donahue
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  • Brian Donahue
    ... or if your Exchange server allows anonymous relay, you don't need a username and password. You just have to allow anonymous relay in Exchange and tell it to allow the Monitor server's IP address to relay mail to your domain.

    http://technet.microsoft.com/en-us/libr ... 32021.aspx
    Brian Donahue
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