Exchange Online Migration: Single Tenant with Multiple Exchange EndpointsExchange 2003 to 2010 Migration...

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Exchange Online Migration: Single Tenant with Multiple Exchange Endpoints


Exchange 2003 to 2010 Migration Backout PlanIntermittent communication issues with Office 365 (Exchange Online)Exchange 2010 to Exchange Online cutover migration errorComplex Exchange 2010 to Office 365 Migration with multiple domainsSimplest way to move a small public folder to Exchange Online?Exchange 2010 to 365 QuestionsCutover migration from exchange 2007 to exchange online errorExchange multi domains hybrid migrationSyncronize Exchange Online account with local exchangeExchange Online Transport Rule













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















    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






      share|improve this question













      share|improve this question











      share|improve this question




      share|improve this question










      asked 3 hours ago









      gravyfacegravyface

      12.3k145494




      12.3k145494






















          1 Answer
          1






          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
            1 hour ago













          • 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
            22 mins ago











          Your Answer








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          1 Answer
          1






          active

          oldest

          votes








          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
            1 hour ago













          • 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
            22 mins ago
















          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
            1 hour ago













          • 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
            22 mins ago














          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 24 mins ago

























          answered 2 hours ago









          MassimoMassimo

          52.9k44165280




          52.9k44165280













          • 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
            1 hour ago













          • 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
            22 mins ago



















          • 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
            1 hour ago













          • 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
            22 mins ago

















          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
          1 hour ago







          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
          1 hour ago















          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
          22 mins ago





          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
          22 mins ago


















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