SMTP Relay Exchange 2010

Hello Everyone,

I have an Exchange 2010 server setup and I installed a ShoreTel phone system yesterday. When it comes to the SMTP feature, I have receive connectors that have been working and we are not an open relay.

For example, the shoretel server smart host set to smtp.office365.com with basic authentication and TLS. If I send it to an email address associated with the O365 account it works to various email accounts except my domain.

Something must be blocking it. I see that the eml message is stuck in the "queue" folder under IIS.

Help please!
ryanbarnes86Asked:
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Will SzymkowskiSenior Solution ArchitectCommented:
Can you test and remove "authentication" add the IP of the shoretel to the list of servers and then test and see if this works? You could also create a New Receive Connector and do the same test.

Will.
ryanbarnes86Author Commented:
hey Will - Thanks for the reply. What kind of receive connector would that look like?
Will SzymkowskiSenior Solution ArchitectCommented:
Do the following...
- Open EMC
- Server Config>Hub Transport
- Create a New Receive Connector
- Create a Custom Connector
- Create a Name for the connector>click next
- specify the FQDN of the mail server
- Receive Mail from the following remote server (enter the IP of the shoretel server)
- Open the new receive connector>click Authentication Tab
- Make sure that TLS is enabled>click on the Permissions Tab
- Make sure that Anonyoums Users, Exchange Users and Exchange Servers are checked

Will.

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ryanbarnes86Author Commented:
Thanks all who helped out. I already had the receive connector setup properly but here is what we ended up doing.

1.) In the ShoreTel Director system, removed the smart host fields.
2.) On the ShoreTel Windows Server (FTP, IIS, Application Server for ShoreTel), I went under IIS 6.0 and made it the relay. by doing the following:
Basic Authentication with credentials for Exchange 2010 with TLS
Unchecked the box under the "Advanced" section for "Delivery" that said send directly to host first.

That was the key... outside the other normal settings ShoreTel recommended. Darn ShoreTel.
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