Best way to migrate Apple Server Mail (10.9) to Exchange 2013?

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SimmZ2008 Author

Level 1

10 points

Best way to migrate Apple Server Mail (10.9) to Exchange 2013?

Well...

I have to migrate mailboxes from an Apple OS-X 10.9 Mail Server (Mavericks) to a Microsoft Exchange 2013 hosting service (Office-365 plan). I have 60 users and few have over 20 Gb of email archives (sorted in many folders) since 5 years or so. By chance our hosting plan allow 50 Gb per mailboxe. We need to keep everything for legal reasons so I had to move everything into Exchange server.

I haven't perform any migration try because we did not receive my Microsoft hosting plan yet (it's in process), but I want to prepare some kind of plan in the meantime! I'm pretty sure I'll need to make export/import manally on every 60 users and this is not an issue. I'm not looking for an automated process absolutely, I just want an effective and reliable process to make things clean and no loose anything.

My first intuition would be to setup both Apple Mail (IMAP) and Exchange 2013 accounts into Microsoft Office 2011 (no Windows in tha' office BTW), thereafter Apple Mail account to complete it's initial cache sync, to run some kind of "EXPORT TO PST" of the entire mailbox. Thereafter there's probably some kind of "IMPORT PST" somewhere that can import mails and folder from the PST to the Exchange account?

I'll need also to migrate iCAL (CalDAV) users calendars to Exchange calendar. Same as Contacts (aka Adress Book) into Exchange contact. But I'm not concerned that much with iCal and Contacts right now, I'm pretty sure the export/import is pretty straight forward...

How do you process yourself? Any clues for me?

Posted on May 27, 2014 11:57 AM

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Answer 1

SimmZ2008 Author

Level 1

10 points

May 28, 2014 8:14 AM in response to SimmZ2008

Really? Nobody try this before?

Just for fun, what do you people do when your business grow up and then the Apple Server became completely overwhelmed? Because there's no mistake, Apple servers are no longer what they were and when the workgroup grow over 20 peoples (or so), the server side of OS-X is quickly overwhelmed! Moreover since OS-X 10.9 (Mavericks), Apple have removed many required business features (such as webmail), which is fairly unusual for a company to removes features instead of adding new!

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Answer 2

bfdulock

Level 2

214 points

May 28, 2014 8:19 AM in response to SimmZ2008

I would normally use IMAP accounts from both servers to allow users to migrate their email/folders between mail servers. However, that is probably not pracitcal for 60 users.

Bryan Dulock

ACN

Houston, TX

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Answer 3

SimmZ2008 Author

Level 1

10 points

May 28, 2014 8:25 AM in response to bfdulock

Well I'm not affraid of the 60 users itself, more by the 30 GB each I would say... hihihihi 😁

How would you make the transfert of folders and mails? With Outlook 2011 and a drag & drop between each other accounts?

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Answer 4

bfdulock

Level 2

214 points

May 28, 2014 8:34 AM in response to SimmZ2008

Yes, using drag & drop with the email client. I am more comfortable with Apple Mail myself, but any client that supports IMAP should work.

I wish I could say their is a more direct way to mass move the email but I don't know of any.

Bryan Dulock

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Answer 5

SimmZ2008 Author

Level 1

10 points

May 28, 2014 8:42 AM in response to bfdulock

I can use Apple Mail too it it makes thing easier at least for the migration part of the job!

I don't like Outlook 2011 myself, but in a Microsoft Exchange environment it's better because it joint all features in one app (email, calendar and contacts). You can make about the same thing with Apple Mail, iCal and Contacts, but in separate ways.

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Answer 6

bfdulock

Level 2

214 points

May 28, 2014 10:39 AM in response to SimmZ2008

Since you are retiring you Mac server you could use it as a mail archive server by preserving your user accounts on it and keeping these IMAP accounts configured in Outlook.

Here is some documentation regarding this:

https://discussions.apple.com/thread/5970763

Bryan Dulock

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Answer 7

SimmZ2008 Author

Level 1

10 points

May 28, 2014 11:11 AM in response to bfdulock

Unfortunately keeping the OS-X Server alive as an archive is not an option because there's major corruptions in this server right now and I need to completely format it and reinstall from scratch once the mail is migrated into Exchange. The problem is the server's datas as been transferred/copied/migrated from an old XServe (10.6 Server) into a Mac Pro Server (Mid-2012 generation, bought in summer 2013), then upgraded to Lion Server and finally to Mavericks Server.

Actually Mail/iCal/Contacts are the last services running on this server (with Open Directory for authentication). After the format/reinstall the OS-X Server will only act as :

- Profile Manager

- Software Update

- Caching

I'll probably use the MacPro (12-core, 32 GB) to video processing and use a MacMini i7 as server.

Everything on the server's side will now be running on few Windows Server 2012 (R2) on a true servers hardware (HP Proliant) incling Active Directory Domain, File Server, Print Server, DHCP, DNS, Terminal Server, VPN, etc. And mail service will be provided by Microsoft Exchange 2013 hosting service (Office 365).

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