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I'm getting ready to upgrade my SBS 2008 box to two Windows Server 2012 R2 VMs. I plan on installing Exchange 2016 on one VM and the DC/file server/update services/a few custom services on the other VM.

I'm not sure the best upgrade path, however. I can't do a direct migration to Exchange 2016 from Exchange 2007. I have a few options, however. Note that we are also using GFI MailEssentials for SPAM and AV.

I could do a PST export, decommission the current SBS, and then recreate the mailboxes on a fresh Exchange 2016 install. Is this sort of thing actually possible? I don't have a cumbersome amount of mailboxes, so I'm not worried about about my time on that account. I am worried about my users keeping all of their settings and whatnot, however.

I could do an intermediate migration to Exchange 2013 and then another migration to Exchange 2016.

I could use a tool like CodeTwo to perform a cross-forest migration. Admittedly, I don't know anything about this tool or even how a cross-forest migration works.

What would likely be the easiest option given my scenario of SBS 2008 to Exchange 2016 with a limited number of mailboxes and public folders and MailEssentials? Will it be possible to get any of these options finished in a single weekend?

I'm just looking for a nudge in the right direction.

  • Add a new server with ad and exchange 2013. Migrate everything to that. Remove sbs, then migrate to your new vms. You can do a lot of work prep work 'live' as it doesn't touch the running set-up – Drifter104 Jan 14 '16 at 9:11
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If you can eliminate the public folders first you will make life a lot easier. However the move through Exchange 2013 first to Exchange 2016. I wouldn't try and do it in a weekend though - it is perfectly possible to do the bulk of the work "live" as already stated, with just a final switch required. I also prefer to have both the old and new server running for a period together to ensure the mailboxes move across correctly and you catch all of the traffic.

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Depends. If you don't have a lot of mailboxes, you can do the good ol' "cold handover" (PST out, PST in). That's the cleanest option, but your users will lose their custom markings, category colors, mailbox rules and outlook profile settings (will have to recreate profile).

The "smoothest" way for your users would be the two-step migration 2008 > 2013 > 2016. The first step will have to be done quickly, because SBS doesn't like to run as not-the-only-DC. If done right, the pressure will be gone after the first step. Nothing will be lost, but that will take more time. Which is no problem, because it an be done live.

If you are going for the PST thing, consider putting them into office365 exchange online.

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