Exchange Online Migration: Single Tenant with Multiple Exchange Endpoints

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2















Planning out a migration for 3 separate Exchange Servers/AD forests with no AD trusts configured; there is site-to-site connectivity by way of IPSec tunnels.



These three mail servers share an email domain by way of Internal Relays (configured for MX lookup, which points to a central ISP-owned Linux mail server with forwarding aliases setup for each recipient's respective Exchange Server).



My question is, can you setup multiple Exchange endpoints for a single Exchange Online tenant? Hybrid Full/Minimal or Cutover? Are there 3rd-party solutions that can do this if not?










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    2















    Planning out a migration for 3 separate Exchange Servers/AD forests with no AD trusts configured; there is site-to-site connectivity by way of IPSec tunnels.



    These three mail servers share an email domain by way of Internal Relays (configured for MX lookup, which points to a central ISP-owned Linux mail server with forwarding aliases setup for each recipient's respective Exchange Server).



    My question is, can you setup multiple Exchange endpoints for a single Exchange Online tenant? Hybrid Full/Minimal or Cutover? Are there 3rd-party solutions that can do this if not?










    share|improve this question
























      2












      2








      2








      Planning out a migration for 3 separate Exchange Servers/AD forests with no AD trusts configured; there is site-to-site connectivity by way of IPSec tunnels.



      These three mail servers share an email domain by way of Internal Relays (configured for MX lookup, which points to a central ISP-owned Linux mail server with forwarding aliases setup for each recipient's respective Exchange Server).



      My question is, can you setup multiple Exchange endpoints for a single Exchange Online tenant? Hybrid Full/Minimal or Cutover? Are there 3rd-party solutions that can do this if not?










      share|improve this question














      Planning out a migration for 3 separate Exchange Servers/AD forests with no AD trusts configured; there is site-to-site connectivity by way of IPSec tunnels.



      These three mail servers share an email domain by way of Internal Relays (configured for MX lookup, which points to a central ISP-owned Linux mail server with forwarding aliases setup for each recipient's respective Exchange Server).



      My question is, can you setup multiple Exchange endpoints for a single Exchange Online tenant? Hybrid Full/Minimal or Cutover? Are there 3rd-party solutions that can do this if not?







      microsoft-office-365 exchange-migration






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      asked Feb 27 at 19:45









      gravyfacegravyface

      12.3k145494




      12.3k145494




















          1 Answer
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          3














          This is possible in general, although quite tricky to get right; here's the only offical documentation I was able to find: https://docs.microsoft.com/en-us/previous-versions/exchange-server/exchange-150/jj873754(v=exchg.150). It refers to Exchange 2013 and it's marked as "no longer updated content", but it should still be valid.



          Here is another unofficial but more recent article:
          https://practical365.com/blog/exchange-multi-forest-hybrid-tips-and-tricks/




          However, you are using the same SMTP domain in all forests, and this adds a whole lot of issues, not only for mail routing (which probably can still be made to work) but mainly for the Autodiscover service, which can't possibly work for all your users in this scenario, since every Exchange forest doesn't know about users in the other ones; and without a properly working Autodiscover service, lots of things are going to break.




          My suggestion would be to perform three cutover migrations in sequence; setting up and running a three-forests hybrid environment where all forests share the same SMTP domain is going to be painful, if it works at all.






          share|improve this answer

























          • Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

            – gravyface
            Feb 27 at 21:01












          • Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

            – Massimo
            Feb 27 at 22:25










          Your Answer








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          1 Answer
          1






          active

          oldest

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          1 Answer
          1






          active

          oldest

          votes









          active

          oldest

          votes






          active

          oldest

          votes









          3














          This is possible in general, although quite tricky to get right; here's the only offical documentation I was able to find: https://docs.microsoft.com/en-us/previous-versions/exchange-server/exchange-150/jj873754(v=exchg.150). It refers to Exchange 2013 and it's marked as "no longer updated content", but it should still be valid.



          Here is another unofficial but more recent article:
          https://practical365.com/blog/exchange-multi-forest-hybrid-tips-and-tricks/




          However, you are using the same SMTP domain in all forests, and this adds a whole lot of issues, not only for mail routing (which probably can still be made to work) but mainly for the Autodiscover service, which can't possibly work for all your users in this scenario, since every Exchange forest doesn't know about users in the other ones; and without a properly working Autodiscover service, lots of things are going to break.




          My suggestion would be to perform three cutover migrations in sequence; setting up and running a three-forests hybrid environment where all forests share the same SMTP domain is going to be painful, if it works at all.






          share|improve this answer

























          • Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

            – gravyface
            Feb 27 at 21:01












          • Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

            – Massimo
            Feb 27 at 22:25















          3














          This is possible in general, although quite tricky to get right; here's the only offical documentation I was able to find: https://docs.microsoft.com/en-us/previous-versions/exchange-server/exchange-150/jj873754(v=exchg.150). It refers to Exchange 2013 and it's marked as "no longer updated content", but it should still be valid.



          Here is another unofficial but more recent article:
          https://practical365.com/blog/exchange-multi-forest-hybrid-tips-and-tricks/




          However, you are using the same SMTP domain in all forests, and this adds a whole lot of issues, not only for mail routing (which probably can still be made to work) but mainly for the Autodiscover service, which can't possibly work for all your users in this scenario, since every Exchange forest doesn't know about users in the other ones; and without a properly working Autodiscover service, lots of things are going to break.




          My suggestion would be to perform three cutover migrations in sequence; setting up and running a three-forests hybrid environment where all forests share the same SMTP domain is going to be painful, if it works at all.






          share|improve this answer

























          • Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

            – gravyface
            Feb 27 at 21:01












          • Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

            – Massimo
            Feb 27 at 22:25













          3












          3








          3







          This is possible in general, although quite tricky to get right; here's the only offical documentation I was able to find: https://docs.microsoft.com/en-us/previous-versions/exchange-server/exchange-150/jj873754(v=exchg.150). It refers to Exchange 2013 and it's marked as "no longer updated content", but it should still be valid.



          Here is another unofficial but more recent article:
          https://practical365.com/blog/exchange-multi-forest-hybrid-tips-and-tricks/




          However, you are using the same SMTP domain in all forests, and this adds a whole lot of issues, not only for mail routing (which probably can still be made to work) but mainly for the Autodiscover service, which can't possibly work for all your users in this scenario, since every Exchange forest doesn't know about users in the other ones; and without a properly working Autodiscover service, lots of things are going to break.




          My suggestion would be to perform three cutover migrations in sequence; setting up and running a three-forests hybrid environment where all forests share the same SMTP domain is going to be painful, if it works at all.






          share|improve this answer















          This is possible in general, although quite tricky to get right; here's the only offical documentation I was able to find: https://docs.microsoft.com/en-us/previous-versions/exchange-server/exchange-150/jj873754(v=exchg.150). It refers to Exchange 2013 and it's marked as "no longer updated content", but it should still be valid.



          Here is another unofficial but more recent article:
          https://practical365.com/blog/exchange-multi-forest-hybrid-tips-and-tricks/




          However, you are using the same SMTP domain in all forests, and this adds a whole lot of issues, not only for mail routing (which probably can still be made to work) but mainly for the Autodiscover service, which can't possibly work for all your users in this scenario, since every Exchange forest doesn't know about users in the other ones; and without a properly working Autodiscover service, lots of things are going to break.




          My suggestion would be to perform three cutover migrations in sequence; setting up and running a three-forests hybrid environment where all forests share the same SMTP domain is going to be painful, if it works at all.







          share|improve this answer














          share|improve this answer



          share|improve this answer








          edited Feb 27 at 22:23

























          answered Feb 27 at 20:17









          MassimoMassimo

          53.1k44168281




          53.1k44168281












          • Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

            – gravyface
            Feb 27 at 21:01












          • Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

            – Massimo
            Feb 27 at 22:25

















          • Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

            – gravyface
            Feb 27 at 21:01












          • Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

            – Massimo
            Feb 27 at 22:25
















          Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

          – gravyface
          Feb 27 at 21:01






          Was thinking the same thing: logistically, being in 3 places at once, would be near impossible anyways. There will be a net new AD forest setup centrally, which is what we will be running DirSync on for password synchronization, but getting all those profiles flipped over is going to be a helluva lot of boot prints...

          – gravyface
          Feb 27 at 21:01














          Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

          – Massimo
          Feb 27 at 22:25





          Yes, migrating everything to a single forest and then going to hybrid is the cleanest solution; I didn't mention it only because I was assuming you didn't want to add another forest to this mess :) But if you have enough time and resources, it's better indeed.

          – Massimo
          Feb 27 at 22:25

















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