SBS 2008 to Server 2019 Essentials migration
Several years ago I did a SBS 2011 to 2019 Standard migration. The problem, of course, was the Exchange portion. I got them over to Outlook 365 before even doing the migration. The problem was the autodiscover always wanted to look for the SBS 2011. I had to do registry entries and hacks to get Outlook working and pointing towards office 365. It was kind of a pain.
So now I have to migrate a SBS 2008 to 2019 Essentials. There are only eight workstations so a completely new domain would not be out of the question. How would you approach the migration and when would you move Exchange server to office 365?
So now I have to migrate a SBS 2008 to 2019 Essentials. There are only eight workstations so a completely new domain would not be out of the question. How would you approach the migration and when would you move Exchange server to office 365?
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@Hypercat I am not migrating Exchange 2007 to 2016 or 2019. I am "migrating" it to Office 365.Exporting and importing PST files is an option.
@MAS I believe I was give that command and many, many more in hope of fixing the autodiscovery problem but it did not help. Since it is a SBS2008 Server the mailboxes obviously are on premise. That is the problem. Workstations on this LAN will autodiscover to the on premise SBS2008 even if the mailboxes have been move to Office 365. It was a royal pain to get Outlook to point to Office 365 while the SBS2008 server existed.
@MAS I believe I was give that command and many, many more in hope of fixing the autodiscovery problem but it did not help. Since it is a SBS2008 Server the mailboxes obviously are on premise. That is the problem. Workstations on this LAN will autodiscover to the on premise SBS2008 even if the mailboxes have been move to Office 365. It was a royal pain to get Outlook to point to Office 365 while the SBS2008 server existed.
ASKER
Can anyone see any issues with essentially starting over? Put together a new server on a different domain and rejoin all workstations to that domain yet keep the exchange server on the existing domain so they can use it until we migrate off.
You don't really need to be on the same domain as the exchange server to access the exchange server you?
You don't really need to be on the same domain as the exchange server to access the exchange server you?
This will be a double task for you.
Please explain what you gain if you migrate to new forest
or explain the idea behind moving to new forest.
Please explain what you gain if you migrate to new forest
or explain the idea behind moving to new forest.
ASKER
The idea is to really start over clean. SBS 2008 puts a whole lot of garbage in the active directory. It arranges OUs in a way that only SBS does. The metadata has more things in it that you want to think about. It throws in a ton of specific SBS policies. It's just a whole lot of garbage that is been collecting since 2008 that is going to be brought over to a new server. There are only eight workstations and they are mostly Windows 7 that are in the same boat.
First of all, you cannot run Exchange 2007 in a Windows 2019 domain. So, if that's what you were thinking, then the answer is a firm "no." It may be possible to allow your workstations to use the Exchange 2007 in the old domain while being joined to the new domain, but it would be clumsy and unnecessary. And you don't want to maintain that going forward anyway, so why not migrate everything at once?
It may be a tossup between the two options, migration or starting over. If you migrate, you may have to do some cleanup; if you create a new domain, you also have to recreate user and computer accounts, printers (if shared), etc.
Personally, I've chosen to migrate from SBS2008 to Server 2019 even in small situations because it does save some work. Instead of having to recreate user accounts and unjoin workstations from one domain and join them to a new domain, you can migrate those aspects of Active Directory along with any other customizations that may have been made that you may want to keep. Once your active directory and FSMO roles are migrated, you're no longer bound by the SBS restrictions and rules, so you can say goodbye to the customized server management console and all the wizards and do your own AD management. Or, after shutting down the old SBS server, you can install Essentials on the 2019 server and go from there. Moreover, you can easily move documents and programs to the new server directly instead of using an external method (i.e., USB sticks) to move data.
When it comes down to it, after migrating to Server 2019 (whether you choose to do Essentials or Standard), it's fairly easily to remove the SBS "junk" (as I like to call it). Simply create your own OU's and group policies or modify the policies and OU's that are in place to fit what you need. Then unlink/disable and delete any policies, OU's, etc., that you're not going to use. Once migrated, user and computer accounts can be moved easily to the default OUs or ones you create yourself, depending on your preference.
It may be a tossup between the two options, migration or starting over. If you migrate, you may have to do some cleanup; if you create a new domain, you also have to recreate user and computer accounts, printers (if shared), etc.
Personally, I've chosen to migrate from SBS2008 to Server 2019 even in small situations because it does save some work. Instead of having to recreate user accounts and unjoin workstations from one domain and join them to a new domain, you can migrate those aspects of Active Directory along with any other customizations that may have been made that you may want to keep. Once your active directory and FSMO roles are migrated, you're no longer bound by the SBS restrictions and rules, so you can say goodbye to the customized server management console and all the wizards and do your own AD management. Or, after shutting down the old SBS server, you can install Essentials on the 2019 server and go from there. Moreover, you can easily move documents and programs to the new server directly instead of using an external method (i.e., USB sticks) to move data.
When it comes down to it, after migrating to Server 2019 (whether you choose to do Essentials or Standard), it's fairly easily to remove the SBS "junk" (as I like to call it). Simply create your own OU's and group policies or modify the policies and OU's that are in place to fit what you need. Then unlink/disable and delete any policies, OU's, etc., that you're not going to use. Once migrated, user and computer accounts can be moved easily to the default OUs or ones you create yourself, depending on your preference.
ASKER
It is almost a two-step operation. The first being to get them on Office 365 for email. The last time I did this I simply disabled the auto discover on the workstations an manually configured Outlook 2007 to point to O365. So initially what I will wind up in "Phase One" is no changes on the workstations with the exception that Outlook 2007 will now point to O365. I believe that is an allowable combination isn't it?
Phase 2 will be moving the data and you are right you just have to decide the best approach. Since there are only eight computers and they are a mess anyway (Windows 7) I would be more inclined to just start with a new domain and new workstations and just bite the bullet.
Phase 2 will be moving the data and you are right you just have to decide the best approach. Since there are only eight computers and they are a mess anyway (Windows 7) I would be more inclined to just start with a new domain and new workstations and just bite the bullet.
Yes - that would be much better than trying to make Exchange 2007 work during the migration from SBS to Windows 2019. If in your (obviously expert in this case) opinion that the workstations as well as the Active Directory will need a LOT of cleanup after migration then going with a clean new domain will probably be best. Moving the data will be a bit of a pain but is easy enough to accomplish. You may still have to clean up things on the workstation side, depending on what the mess consists of! Have they considered upgrading their Win7 workstations to Win10?
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Please check step1 and 2.
https://www.experts-exchange.com/articles/31221/Fix-for-Exchange-server-2016-2019-certificate-and-related-issues.html