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Office 365 Exchange Online Migration from Exchange 2007 Requires SSL Certificate But Local Domain is .com suffix we do not own

Posted on 2016-07-18
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Last Modified: 2016-07-27
Hey guys and gals I'll try to make this as concise and coherent as possible.

We currently have an Exchange 2007 box in a 2008 r2 active directory domain. We're wanting to migrate to Office 365 with Exchange online. Reviewing the documentation it looks like they want "exchange anywhere" enabled to migrate our exchange database which requires a valid SSL certificate. My problem is that when the local domain was created it was created as "City.Contoso.com". The issue is we do not own Contoso.com and the cost to acquire that domain is incredibly out of budget.  So we've been just self-signing but it's now hit a breaking point. How do I possibly get a certificate to work with this exchange server to enable the services required to migrate this EDB?

Thank you so much for your help!
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Question by:bubearjr
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Expert Comment

by:Simon Butler (Sembee)
ID: 41717890
They need an SSL certificate that works outside.
You must have your own domain, so configure Exchange to use that instead. The internal domain doesn't matter.

Setup a split DNS system so host.example.com resolves internally to the Exchange server, as well as externally and get an SSL certificate for host.example.com.
Then change the URLs within Exchange. http://semb.ee/hostnames2007

The feature you need to enable is Outlook Anywhere, not Exchange anywhere.

If the domain really is contoso.com (rather than you using that as a placeholder) then you would never get contoso.com as it is Microsoft's domain.
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Author Comment

by:bubearjr
ID: 41719624
Would a better choice simply to just be to get a tool to migrate the mailboxes instead of fussing with all of this? This whole issue is purely to dump my on site exchange box at the end of the day.
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Expert Comment

by:Simon Butler (Sembee)
ID: 41719739
A suitable certificate will cost you $20 if you look around.
A tool isn't going to make it easier.

You cannot have been using the server remotely at all - an SSL certificate isn't really an optional function for Exchange 2007 and higher. to use Exchange properly you need a certificate.
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bubearjr earned 0 total points
ID: 41723294
I was using it with OWA and mobile devices without a valid certificate. I contacted CDW and they get me skykick which does solve my problem so a tool was the easiest work around.
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Author Closing Comment

by:bubearjr
ID: 41730938
Using a third party tool has really made the entire process much simpler.
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