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Address Rewriting not working on outbound mail

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Hello, I have setup an Edge Transport server between Office 365/EOP and our internal mail servers (Non-Exchange). For this, I have setup two receive connectors and two send connectors on the Edge server. Mail flow in and out is working fine.

I enabled Address Rewriting agents for both inbound and outbound. Then I made an address rewrite entry. The entry works fine for inbound mail. The address @contosco.com is changed to @anotherdomain.com and routed appropriately. However, when I send an email from @anotherdomain.com back to outside word, it is not rewritten to @contosco.com. 

Here are the commands I used to setup the connectors:

New-ReceiveConnector -Name "From Internal to Edge" -Usage Internal -AuthMechanism ExternalAuthoritative -PermissionGroups AnonymousUsers, ExchangeServers -RemoteIpRanges <Internal Subnets> -ProtocolLogging Verbose
New-SendConnector -Name "From Edge to Internal" -Usage Internal –AddressSpaces <domains> -ProtocolLogging Verbose
New-SendConnector -Name "From Edge to EOP" -AddressSpaces * -RequireTLS $True -SmartHosts <organization>.mail.protection.outlook.com -ProtocolLogging Verbose
New-ReceiveConnector -Name "From EOP to Edge" -Usage Custom -AuthMechanism TLS  -PermissionGroups AnonymousUsers -RemoteIpRanges $ip.DataCenterIPs -RequireTLS $True -Bindings <ip address of server>:25 -ProtocolLogging Verbose

Note that EdgeSync is not used as the internal mail servers are not Exchange only.

Any ideas?



Rishi


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