Exchange Hybrid Migration












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Apologies if this question has been answered before. We are going for Exchange hybrid migration to EOL (Exchange Online). On-premise, we have Exchange 2016 mailbox and Exchange 2016 Edge transport servers, DLP appliance (Forcepoint 8.4) and Cisco Email Security as our mail gateway.



We are enabling Centralised Mail Transport (CMT) because we wish to retain the DLP appliance for now until all mailboxes are migrated.



1) When running the HCW, should I choose the Edge Transport server as the Optimal server or the Exchange 2016 mailbox server? The Edge Transport server is used for address-rewrite for outgoing emails. Incoming emails do not traverse the Edge Transport server.



2) Is there any additional configuration needed on the send/receive connectors, so that email delivered to the online mailbox is routed back to the on-premise Exchange (CMT) without issues. I read somewhere that you should not have anything in between the on-premise Exchange and EOL that modifies the email.



3) Is there any address rewriting capabilities in Exchange Online?



Thank you.










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migrated from superuser.com Jan 26 at 22:49


This question came from our site for computer enthusiasts and power users.























    0















    Apologies if this question has been answered before. We are going for Exchange hybrid migration to EOL (Exchange Online). On-premise, we have Exchange 2016 mailbox and Exchange 2016 Edge transport servers, DLP appliance (Forcepoint 8.4) and Cisco Email Security as our mail gateway.



    We are enabling Centralised Mail Transport (CMT) because we wish to retain the DLP appliance for now until all mailboxes are migrated.



    1) When running the HCW, should I choose the Edge Transport server as the Optimal server or the Exchange 2016 mailbox server? The Edge Transport server is used for address-rewrite for outgoing emails. Incoming emails do not traverse the Edge Transport server.



    2) Is there any additional configuration needed on the send/receive connectors, so that email delivered to the online mailbox is routed back to the on-premise Exchange (CMT) without issues. I read somewhere that you should not have anything in between the on-premise Exchange and EOL that modifies the email.



    3) Is there any address rewriting capabilities in Exchange Online?



    Thank you.










    share|improve this question













    migrated from superuser.com Jan 26 at 22:49


    This question came from our site for computer enthusiasts and power users.





















      0












      0








      0








      Apologies if this question has been answered before. We are going for Exchange hybrid migration to EOL (Exchange Online). On-premise, we have Exchange 2016 mailbox and Exchange 2016 Edge transport servers, DLP appliance (Forcepoint 8.4) and Cisco Email Security as our mail gateway.



      We are enabling Centralised Mail Transport (CMT) because we wish to retain the DLP appliance for now until all mailboxes are migrated.



      1) When running the HCW, should I choose the Edge Transport server as the Optimal server or the Exchange 2016 mailbox server? The Edge Transport server is used for address-rewrite for outgoing emails. Incoming emails do not traverse the Edge Transport server.



      2) Is there any additional configuration needed on the send/receive connectors, so that email delivered to the online mailbox is routed back to the on-premise Exchange (CMT) without issues. I read somewhere that you should not have anything in between the on-premise Exchange and EOL that modifies the email.



      3) Is there any address rewriting capabilities in Exchange Online?



      Thank you.










      share|improve this question














      Apologies if this question has been answered before. We are going for Exchange hybrid migration to EOL (Exchange Online). On-premise, we have Exchange 2016 mailbox and Exchange 2016 Edge transport servers, DLP appliance (Forcepoint 8.4) and Cisco Email Security as our mail gateway.



      We are enabling Centralised Mail Transport (CMT) because we wish to retain the DLP appliance for now until all mailboxes are migrated.



      1) When running the HCW, should I choose the Edge Transport server as the Optimal server or the Exchange 2016 mailbox server? The Edge Transport server is used for address-rewrite for outgoing emails. Incoming emails do not traverse the Edge Transport server.



      2) Is there any additional configuration needed on the send/receive connectors, so that email delivered to the online mailbox is routed back to the on-premise Exchange (CMT) without issues. I read somewhere that you should not have anything in between the on-premise Exchange and EOL that modifies the email.



      3) Is there any address rewriting capabilities in Exchange Online?



      Thank you.







      email exchange






      share|improve this question













      share|improve this question











      share|improve this question




      share|improve this question










      asked Jan 26 at 4:42









      RNathanRNathan

      61




      61




      migrated from superuser.com Jan 26 at 22:49


      This question came from our site for computer enthusiasts and power users.









      migrated from superuser.com Jan 26 at 22:49


      This question came from our site for computer enthusiasts and power users.
























          1 Answer
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          0














          1) Edge server.



          2) No. When you add an Edge Transport server to your hybrid deployment, it communicates with EOP on behalf of the internal Exchange servers. The Edge Transport server acts as a relay between the internal Exchange servers and EOP for outbound messaging from the on-premises organization to the Exchange Online organization.



          If you need to delete and recreate an Edge subscription that's used to communicate between your on-premises organization and Exchange Online, make sure to run the Hybrid Configuration wizard again.



          3)No. We must use Edge server for address rewriting.






          share|improve this answer
























          • Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

            – RNathan
            Feb 3 at 2:06











          • Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

            – RNathan
            Feb 7 at 8:07













          • Thanks for sharing.

            – Jayce Yang
            Feb 12 at 6:21











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          1 Answer
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          1 Answer
          1






          active

          oldest

          votes









          active

          oldest

          votes






          active

          oldest

          votes









          0














          1) Edge server.



          2) No. When you add an Edge Transport server to your hybrid deployment, it communicates with EOP on behalf of the internal Exchange servers. The Edge Transport server acts as a relay between the internal Exchange servers and EOP for outbound messaging from the on-premises organization to the Exchange Online organization.



          If you need to delete and recreate an Edge subscription that's used to communicate between your on-premises organization and Exchange Online, make sure to run the Hybrid Configuration wizard again.



          3)No. We must use Edge server for address rewriting.






          share|improve this answer
























          • Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

            – RNathan
            Feb 3 at 2:06











          • Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

            – RNathan
            Feb 7 at 8:07













          • Thanks for sharing.

            – Jayce Yang
            Feb 12 at 6:21
















          0














          1) Edge server.



          2) No. When you add an Edge Transport server to your hybrid deployment, it communicates with EOP on behalf of the internal Exchange servers. The Edge Transport server acts as a relay between the internal Exchange servers and EOP for outbound messaging from the on-premises organization to the Exchange Online organization.



          If you need to delete and recreate an Edge subscription that's used to communicate between your on-premises organization and Exchange Online, make sure to run the Hybrid Configuration wizard again.



          3)No. We must use Edge server for address rewriting.






          share|improve this answer
























          • Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

            – RNathan
            Feb 3 at 2:06











          • Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

            – RNathan
            Feb 7 at 8:07













          • Thanks for sharing.

            – Jayce Yang
            Feb 12 at 6:21














          0












          0








          0







          1) Edge server.



          2) No. When you add an Edge Transport server to your hybrid deployment, it communicates with EOP on behalf of the internal Exchange servers. The Edge Transport server acts as a relay between the internal Exchange servers and EOP for outbound messaging from the on-premises organization to the Exchange Online organization.



          If you need to delete and recreate an Edge subscription that's used to communicate between your on-premises organization and Exchange Online, make sure to run the Hybrid Configuration wizard again.



          3)No. We must use Edge server for address rewriting.






          share|improve this answer













          1) Edge server.



          2) No. When you add an Edge Transport server to your hybrid deployment, it communicates with EOP on behalf of the internal Exchange servers. The Edge Transport server acts as a relay between the internal Exchange servers and EOP for outbound messaging from the on-premises organization to the Exchange Online organization.



          If you need to delete and recreate an Edge subscription that's used to communicate between your on-premises organization and Exchange Online, make sure to run the Hybrid Configuration wizard again.



          3)No. We must use Edge server for address rewriting.







          share|improve this answer












          share|improve this answer



          share|improve this answer










          answered Jan 28 at 3:25









          Jayce YangJayce Yang

          744




          744













          • Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

            – RNathan
            Feb 3 at 2:06











          • Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

            – RNathan
            Feb 7 at 8:07













          • Thanks for sharing.

            – Jayce Yang
            Feb 12 at 6:21



















          • Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

            – RNathan
            Feb 3 at 2:06











          • Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

            – RNathan
            Feb 7 at 8:07













          • Thanks for sharing.

            – Jayce Yang
            Feb 12 at 6:21

















          Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

          – RNathan
          Feb 3 at 2:06





          Thanks. The edge transport only processes outgoing emails for address rewriting. So, is it ok to set this one up as the "hybrid server"?

          – RNathan
          Feb 3 at 2:06













          Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

          – RNathan
          Feb 7 at 8:07







          Thanks Jayce, we have a DLP appliance on prem and most of the users are using IronPort as gateway. That's why I chose Centralised Transport. They are not prepared to decom their legacy stuff at the moment. The Edge server only does outgoing mail. Incoming is straight to the Exchange 2016. We will be turning off the Edge transport server so we will use IronPort for the address rewriting

          – RNathan
          Feb 7 at 8:07















          Thanks for sharing.

          – Jayce Yang
          Feb 12 at 6:21





          Thanks for sharing.

          – Jayce Yang
          Feb 12 at 6:21


















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