How to Migrate email accounts (including emails) from a MAC Server 10.7.5 to a Windows Exchange Server 2010

We have situation where we need to move all user mail accounts from a Mac Mini server used as a mail server to an SBS2011 server with exchange 2010.

Basically we nee to export the users accounts (emails) from the Mac Server and import them into The Windows Exchange Server.

The email accounts at the moment are configured as IMAP.

Has anyone done the same or similar migration before or knows how to? or has any idea where to find the necessary information?

Or if there is a tool to aid in this task?

Thank you in advance for your assistance.

Regards
Stefano
bidoneAsked:
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Marshal HubsEmail ConsultantCommented:
@bidone,

Let me know Which Mac mail application you are using !
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bidoneAuthor Commented:
On the server (a Mac mini i7 2GHz 1 Processor) they are just using the built in mail service, from what I can gather it is Mail Ver 5.3. The Server OS is 10.7.5.

The users computers are a mix of iMacs and MacBooks pro and air, all relatively new with Mac OS X 10.7 and 10.8 all using Mail (the mail program that comes with the mac os.) the version is also mostly 5.3

No 3rd parties mail programs are used.
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Marshal HubsEmail ConsultantCommented:
@bidone,

I am not mac expert but just finding solution, As per my understanding you are using Apple mail which is integrated with  Mac OS X 10.7 and 10.8. So if you are using apple mail application then you can convert your Apple mail mailbox to Mac outlook 2011 use of any third party tool like .Stellar Apple Mail to Outlook 2011 Converter

After the success conversion you can easily sync your Outlook 2011 with exchange 2010 as you want : http://hosting.intermedia.net/support/kb/?id=2101

PS: Use any third party tool on your risk.
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bidoneAuthor Commented:
Thank you Marshalhubs, we will purchase the 3rd party application and follow the instruction as per your links and will let you know how it turns out.

It is still a long process as it has to be done on each individual user computer. I was hoping that there was a 3rd party solution or method that could be run from the server end for all the accounts but if there is not one I will have to factor in the time needed to convert every account individually.

I wait and see if anyone else has any other suggestions in the mean time. I will hold on, on awarding the points until we have tested the solution.

Thank you again for your suggestions.
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Eoin OSullivanConsultantCommented:
@bidone

If all the Mac client computers are using IMAP and ALL their emails are still stored on the Apple Mail Server .. then it makes more sense to go straight from the Mail Server to the Exchange server rather than having to EXPORT the mailboxes from every single individual client Mac computer.
The software recommended by Marshalhubs is only relevant if you're going to buy Outlook 2011 for all your Mac users which will cost $$ and is not necessary.

Apple Mail supports Exchange 2010 mailboxes so you could create all the same user accounts on the new Exchange 2010 server and add the 2nd account into each mail client so now they have the IMAP folders from the Apple Mail Server and the new Exchange Mailbox.  They can simply drag & drop the folders from Apple Mail to Exchange and it will be copied onto the new server.  

Meanwhile all the new emails come into the Exchange Inbox and the old Apple Mail Server accounts can be archived.

You could give users a pre-defined period of time to copy over all their emails before you shut down the old Mac Mini Mail Server.
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Marshal HubsEmail ConsultantCommented:
@bidone,

I think you should go with @eoinosullivan, Because he is an expert in Mac. I have already said i am not an expert in Mac. So just try it. It was good learning for me in Mac OS

Thanks
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bidoneAuthor Commented:
Thank you eoinosullivan and Marshalhubs for your sugestions.

Excuse me for not giving more details about this scenario.

The current environment is all Mac OS server and Computers, all using Mac Mail with the IMAP protocol.

The problem is that the mac mini mail server keeps failing the mail service and does not send emails sometimes 8 to 9 hours later, iCalander appointment tend to disappear or not propagate and be received by the other parties.

So the decision was made to dump the Mac Mini Mail Server and instead introduce a Windows Exchange Mail server on the network.

We will have to create all new accounts on the new server for all the users with their current email address.

Also all Mac computers already have Outlook 2011 installed on their macs but not used, so there is no extra costs there.

So if I take eoinosullivan suggestion, we should do the following:

- Setup the new exchange server onto the existing network and create the user accounts with their current emails as exchange emails accounts.
- Maintain the Mac Mini Mail server running in parallel.
- Create IMAP accounts on outlook 2011 in order to import the existing emails from the Mac Mail Server
- Instruct the users to move (Drag and Drop) the IMAP folders created in Outlook into their equivalents under their exchange mail folder in outlook 2011.
- Change the MX record to point to the new exchange server so all new emails are received by the new server.

Is this a possible solution?
Will Outlook 2011 will be able to import the user current emails from Mac Mail or do I still have to do the export and import instruction that Marshalhubs mentioned above?

Mind you all the emails are on the same computer for each user.

Thank you again for your assistance.

Regards
Stefano
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bidoneAuthor Commented:
Sorry forgot to also mention the another reason that we want to move to Outlook 2011 is that it has better integrated calendar and the sharing of the calendars with other user is easier for us.
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Eoin OSullivanConsultantCommented:
@bidone

It is good to get all the detail as it makes it easier to offer you suggestions.

To drag and drop emails you need to have BOTH accounts setup in the same email client therefore your suggested solution needs a little adjustment.

The setup of the exchange server and mx records etc is fine BUT you should add the new exchange account into Apple Mail so that users can copy the emails across.

If you also setup the new exchange account in Outlook then users can begin to use Outlok for mail and calendars but will have to open apple mail to migrate their older mail.
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bidoneAuthor Commented:
Hello eoinosullivan,

Thank you for your correction, it makes more sense :)

Let me see if I got this right.

- Setup and configure the new Exchange server.
- Create an exchange email account on apple Mail connecting to the new exchange.
- This presents the situation that both the IMAP and Exchange account are in the same Mail program.
- Move (drag and drop) the emails from the IMAP account within Mac Mail into the newly created exchange emails account created also in the Mac Mail program.
- Once this is done then create the same exchange account in Outlook 2011 and the emails should automatically download and populate the folders in outlook in the Mac computer.

Did I understand this correctly?

Would this be the easiest way of doing it? even the fact that will have to be done on each individual machine?

Maybe one day someone will come up with a simple tool that would simple query either database on the relevant mail servers and allow you to transfer the information in both directions... or is it wishful thinking?

Thank you again for your valuable help.

Will keep you posted. But let me know if you think of any other possible solution.

Regards
Stefano
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Eoin OSullivanConsultantCommented:
@bidone

YES - your process is correct.  You don't have to wait until all the mails have been copied over to setup Outlook.  You could setup the exchange account on Outlook at the same time as you are setting it up in Apple Mail.  It is then the user's responsibility to use Apple Mail to copy over their emails & folders .. Outlook will get the updates as they make the transfers in Apple Mail.  In this way you can encourage them to begin using Outlook sooner rather than waiting.

I would recommend that you setup one account and run through the process to check it all runs smoothly.  I'd also recommend that users don't try and copy GBs of data in one attempt from one account to the other as it could put a big strain on the system.  They should transfer the emails in batches ... just in case there are any network outages or dropped connections which interrupt transfers.

I'm not an EXCHANGE expert but I'm not aware of any tool to directly import mailbox accounts from a 3rd Party IMAP server (which would be a much better solution).  There are tools to perform cleanups on user folders where they've been imported from PST files previously associated with IMAP accounts but that is not the same thing.  

It might be worth firing an email off to MS Exchange Forums to see are there any other options.  

I'd recommend you DO NOT mention Apple Mail Server as a lot of MS experts will switch off.  You've noticed NO replies here from MS Exchange experts!!

Just say you want to import IMAP mailboxes from a Linux Mail Server (OSX Server uses 2 programs Postfix and Cyrus to provide the mailboxes and IMAP services which are common to many other Linux systems)
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bidoneAuthor Commented:
Thank you eoinosullivan,

We already intended to do one computer as a test  to make sure it all works.

When it come to Exchange we have all the required knowledge in-house, no problems there if we need to do anything in particular.

My question now is what is the best way of moving not just the emails from Mac Mail to Outlook but also iCal events into Outlook and the Contact into Outlook.

We may have to use some of those tools mentioned above to make it easier to combine all the information.

What's your suggestion on this?

Thank you again for your help.

Regards
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Eoin OSullivanConsultantCommented:
There are several posts here on EE that cover importing iCal & Contacts into Outlook.

iCal you can export all calendars as an .ics file and import into Outlook.
Contacts you can export the contacts as a .vcf file and drag into outlook.

Covered in more detail by Microsoft
http://office.microsoft.com/en-ie/mac-outlook-help/import-ical-or-address-book-items-into-outlook-HA102928319.aspx
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bidoneAuthor Commented:
Because we are not ready to test this at the moment and don't want to leave the question open, I will assign the points to the proposed solution above as in theory should work fine and also we are going to use some of the 3rd parties application suggested above to help with the migration.

Once we have completed the task I will reopen this question so I can add the final comment on the solution.

Thank you to everyone for your suggestions.
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