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We currently have Exchange 2010 running on Windows Server 2008 R2. Our Active Directory is also on the same server. We have 2 mailbox databases and approximately 300 mailboxes. We want to move this exchange server from our self-hosted setup to AWS. I believe one option is to use a 3rd party tool to full replicate the server and update DNS entries (that is a high level view of that option). I am not clear if this will work or not. One other option is to create a new VM at AWS and setup exchange 2010 and migrate or move mailboxes to that new server. I am not 100% sure on the impact this will have on Active Directory. Can anyone advise if they have done this before and what strategy they found worked best for them?

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    Please hire a consultant for such, we miss too much detail and can lead to a disaster if we dont answer correctly. – yagmoth555 Aug 10 '17 at 17:16
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    Most people are moving exchange to Office 365 and Microsoft is definitely moving in that direction. They will push people out of onpremise installations eventually. You can count on it. And for the price, there is little reason not to make the move. Simple migration too. Just my two cents. – Appleoddity Aug 10 '17 at 18:12
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    Why AWS? That doesn't seem to be the right move. – ewwhite Aug 10 '17 at 18:33
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    Honestly, you'd be better served moving to Exchange Online/Office 365. – joeqwerty Aug 10 '17 at 21:44
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Please keep noted that running an Exchange Server on a domain controller (it hosts your Active Directory) isn´t really supported. Additional Exchange 2010 is very old and will be end of life in 2020. You also need to adjust the mailflow here, so some emails will still come into your environment and will be send out (during your "migration windows"). So you need to adjust the MX records and SPF records, however this caused DNS replication delays and some MX server will still try to send emails to your old Exchange Server (old IP) and not the new Exchange Server (with the new IP).

So I would use that project and would do the following:

  • Setup an Exchange 2016 Server, configure it to handle the Exchange 2010 traffic (configure it to handle user and emails; DNS + SPF & MX records needs to be adjusted), then migrate the Exchange 2010 mailboxes (here is an howto). This can be done without any "strange" 3rd party software. You can use the Microsoft way to move user mailboxes from Exchange 2010 to 2016 e.g. on the weekend. Once done remove the Exchange 2010 server.
  • Setup an additional Domain controller and then move the roles to that one, do not leave it running on the Exchange server. You can use this approach also to jump to a higher OS here (e.g. Windows 2012 R2)

So it might be useful to hire an consult here as this isn´t an easy approach and often some dependencies are overseen because the experience to run such a project is missing"

Offtopic (but added for completeness): By the way the best way in your way (very small Exchange Server) would be to move to Exchange Online (part from Office 365). Then there would be no need to host any Exchange Server and make sure its patched with Security updates. It might be easier to setup an Exchange Hybrid server here, then use the way mentioned above to move mailboxes via the Microsoft way.

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