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SBS 2011 to Exchange 2016 RRS feed

  • Question

  • I have a client with a SBS 2011 server (Exchange 2010 on SBS)

    They have 70 users on user CALs and bunch more users on device CALS  (shop people who all share a single system)  We have had a long discussion on the pros and cons of going to O365/Server Essentials vs self-host and they have decided to self-host.  (BTW my last regular-office to O365 migration was 25 seats and the moment it was done the customer said "wham bam thank you mam" and found some El-Cheapo  O365-only-IT-Consulting-group in the city since all the knotty problems had been solved, so I'm not exactly very charitable towards O365 although that is neither here nor there for this customer)

    I've done a significant Exchange 2010 to Exchange 2016 already (300 users) online mailbox migration in a standard non-SBS environment.  I also did (several weeks ago) a SBS 2011 migration for 30 users to Exchange 2016 where I created a new domain, installed into that then moved all mailboxes to pst and then moved the clients to the new domain and imported the psts  That went off without a hitch although it was a lot more work than an online mailbox migration.  I did NOT use a CA on that one although I did use a self-signed cert - but I didn't need to since I set the new AD name to foo.customerdomain.com and the mailserver to mail.foo.customerdomain.com  (I guess I'm a cheap B-T since that saved the customer the yearly fee for the commercial cert)

    This client does not want to do a new domain they want a migration (although they are using the suboptimal .local internal AD suffix)  They are used to the rigmarole of distributing self-signed CA certs and so on.

    They are at 2003 Forest and 2003 Domain mode.  They have 1 2008R2 DC as a secondary DC.  They have no 2003 DC's

    My question is how many people have done this and what pitfalls do you forsee?

    I know some of them already.  First, SBS puts a lot of garbage into the AD that there seems to be no way to remove.  I don't suppose it will matter to leave the user objects in where they are already but it does uglyify the AD  (one of the reasons the only one of these I've done already was NOT a migration)

    Second SBS has that silly "network report" that it emails out (which the site contact is used to getting and will squawk when that goes away)  Suggestions on replacing that would be appreciated.  They also use the Remote Desktop Web feature in SBS so I'll have to enable that on a machine somewhere.  Fortunately they do not use SharePoint or any of that.

    This SBS server used to be where all their files were stored, a couple months ago they bought a new server for fileserving only and I moved all files to that, and setup a GPO to push out their drive letter mappings.  (and of course there were a million shortcuts and other junk pointing to this server which I had to find and change)

    My plan is to setup a new 2016 server hyperv host, then setup 2 virtual servers on it, one a DC and one Exchange.  I'll install CA services on the DC.  Then migrate over the mailboxes, uninstall Exchange, move printer objects off SBS, then demote the DC by then I assume the SBS server will be completely trashed.

    If I raise forest/domain functional level to 2008R2 will it blow up Exchange 2010?  What will it blow up?

    Is renaming the domain to foo.theirdomainname.com even an option or is that asking for nightmares?

    Clients are a mix of win10, win7, Outlook 2010, 2013, 2016, 2019.  All clients are Home & Business licenses purchased from Dell and over-the-counter.  They are on a "when it needs it" machine rotation which means if a machine bites it, they buy a new one to replace it.  Machines are mostly Dell Optiplexes but there's some older Vostros in there.

    Other servers are Server 2008R2 and 1 Server 2003 but that one isn't a DC nor is it that important.

    I've already seen

    https://windowsserveressentials.com/2017/03/28/migrate-sbs-2011-standard-to-windows-server-2016/

    lots of good info there.

    Sunday, October 20, 2019 10:25 PM

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