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?

Hi 

Try  running the below commands and see  that the address rewrite entry outbound agent is enabled 

Get-AddressRewriteEntry
Get-AddressRewriteEntry "Rewrite Contoso.com to Northwindtraders.com" | Format-List

There is no way to disable the outbound agent on a Address Rewrite Entry. You can enable or disable the inbound by use the flag -OutboundOnly to $true or $false. Changing that setting makes no difference to outbound mail.

Here are the results when I run the Get command

[PS] C:\Windows\system32>Get-AddressRewriteEntry -Identity "Rewrite This" | fl


InternalAddress   : xxx@contoso.com
ExternalAddress   : xxx@anotherdomain.com
ExceptionList     : {}
OutboundOnly      : False
AdminDisplayName  :
ExchangeVersion   : 0.1 (8.0.535.0)
Name              : My Venue Photos
DistinguishedName : CN=My Venue Photos,CN=Email Entries,CN=Address Rewrite Configuration,OU=MSExchangeGateway
Identity          : CN=My Venue Photos,CN=Email Entries,CN=Address Rewrite Configuration,OU=MSExchangeGateway
Guid              : c1c72ede-4906-437a-985c-980547083514
ObjectCategory    : CN=ms-Exch-Address-Rewrite-Entry,CN=Schema,CN=Configuration,CN={FC0B799A-A64B-4A2F-BA0D-AF0D1646F37
                    5}
ObjectClass       : {top, msExchAddressRewriteEntry}
WhenChanged       : 3/27/2015 2:27:53 PM
WhenCreated       : 3/25/2015 10:45:45 AM
WhenChangedUTC    : 3/27/2015 7:27:53 PM
WhenCreatedUTC    : 3/25/2015 3:45:45 PM
OrganizationId    :
OriginatingServer : localhost
IsValid           : True
ObjectState       : Unchanged