Options for Moving/Merging an Existing SBS 2008 Server With an Existing SBS 2011 Server

I have a customer with an existing SBS 2008 server in production that will be merging with a company running an SBS 2011 server ...also in production.

We originally planned to manually move all of the SBS 2008 Exchange data to the SBS 2011 server via PSTs, and recreate all the user accounts manually on the SBS 2011 server, since there's no way to do a true migration with the SBS 2011 box already in production. We'd then just scrap or repurpose the SBS 2008 box with a standard flavor of Windows OS.

The messy part, as we see it, will be the calendaring issues that come along with PSTs. I do not know of a way, in this scenario, to avoid the problem with all calendar entries getting appended with "copy" and losing the "originator" info. The calendar entries are pretty important to the SBS 2008 company since they rely on them for several deadlines several months in advance, with several employees tied to them. It will be a PIA to have to manually recreate the entries and re-invite all of the staff. It's like hundreds to thousands of entries.

So... does anyone know of a tool or something that can get around this?

Otherwise, we considered moving both companies to Office 365 mail and using the migration tool that Microsoft provides for Exchange Online... which, we think will work to avoid the calendar issues, but will essentially force them to kill the services on a working Exchange 2010 server (running on the SBS 2011 server). Or... just move both companies over to a single Server 2012 Essentials server.  

Any words of wisdom?
philodendrinAsked:
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Adam BrownSr Solutions ArchitectCommented:
I could give you a third option: Use a third party tool to migrate the mailboxes from one SBS server to the other. MigrationWiz is a good solution I've used a lot. Binary Tree is one my company is examining now. There are a few others out there. Just search for exchange email migration software.

http://www.migrationwiz.com
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philodendrinAuthor Commented:
I thought of that as well, and looked at sbsmigration.com. But, I didn't think the scenario I'm faced with was supported. I will do some further inquiring. The majority of scenarios seemed to rely on the fact that a non-production server would be on the receiving side. I've emailed the folks at migrationwiz.com to see what is or isn't supported with their toolset.
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Adam BrownSr Solutions ArchitectCommented:
As long as there is a public dns record that points to the non production server migrationwiz should work. You could just create a temporary one and make the non production server accessible on the internet through https and it would be enough. Run a search on binary tree's migrator. They have a server based system that might work better in your scenario.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
One way you can avoid the problem you are concerned about with regards to calendaring issues is to temporarily migrate your SBS 2008 mailboxes up to Office365 (using a trial account -- which will have a 25-user limit, but otherwise will work fine).

Then migrate back into your on-premise SBS 2011 with Exchange 2010 by following this guide:
http://www.msexchange.org/articles-tutorials/office-365/exchange-online/migrating-standalone-office-365-tenant-exchange-2010-part1.html

Yep, it's really complex to do it that way.

The other option would be to contact SBSMIGRATION.com as you had considered.  There are NO unsupported scenarios for them (as long as the end result is a supported one --- ie, not trying to get two sbs's to be in the same domain).  They will work with you to achieve what you want to do -- and they have some special tools which make things like this work much more easily.

Jeff
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philodendrinAuthor Commented:
Thanks, Jeff. I was wondering if you could migrate to the cloud and back again. That may be the way we go with this customer. It's still very much in the planning stage.

Regardless of how we do this, we plan on doing quite a lot of trimming/archiving on the larger mailboxes to get them ready for the migration. That way, we're not in a situation where we're stuck watching a 15GB mailbox over a T1 take a week to upload.

I contacted SBSMigration.com earlier this week and haven't heard back yet... but, will hopefully get some more details on how their kit will get around the issues.

I also have been in touch with and received some decent information from migrationwiz.com. The process through Migrationwiz seems pretty straightforward and it only deals with Exchange... which is preferable for us. Since their process copies the data from source to destination... I'm still waiting on confirmation that their tool somehow gets around the calendar issues. We'll likely have to run some tests before we endorse their method/tool. Their pricing is unbelievably low, so I'm quite curious to see if it works and what issues we come up against.

Thanks to all for the suggestions thus far.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
MigrationWiz may work just fine for you... they will automate the process using their own servers instead of pushing things through Office365 as I suggested -- essentially the same method though.

It does work, and yes their pricing is based on the fact that they do a ton of volume.  

Jeff
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philodendrinAuthor Commented:
Jeff... regarding MigrationWiz... this is from their documentation.

The following is a list of items that we do not migrate between mailboxes due to API limitations:

•Items that do not match folder types (i.e. calendar responses within a mail folder)
•Calendar notifications such as invites, cancellations, etc.
•Acceptance status for meeting participants (ex: accepted, declined, tentative)

I'm not entirely sure how to interpret these items. If the calendar invites have already been accepted/declined/marked tentative, I'm assuming that those entries will carry over to calendars without limitations. I'm hoping that what they're talking about here are calendar invites that have not been processed and are sitting in user mailboxes... and the email confirmations that go along with responses.
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Adam BrownSr Solutions ArchitectCommented:
That is correct.

Also, as a note, i have read that adding the legacy exchange dn value in the mailboxes in the old forest to the list of email addresses on the new forest mailbowxes ill allow proper ownership changes to occur on calendar items. I haven't tested that, though.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Since the calendar issue is very important to this organization, I'd suggest that you just do a test of both methods.  MigrationWiz allows you a free account to test a single mailbox.  Easiest way to find out would be to just do it.

Jeff
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