Migrating tricky mailbox from apple outlook 2011 into Office 365

Hello Experts,
We are using a toolkit to transfer our clients onsite exchange into Office 365 , there are about 125 mailboxes . There is one mailbox that isnt completely transfering. When we try to sync that particular mailbox to office 365 it shows lots of errors and Office 365 rejects about 2000+ items. The problematic mailbox is on an apple with Microsoft  2011 office. The whole environment is windows network.
In the past we had a EDB corruption on the exchange and this could be the root cause.  We are wondering is there a way that we can clone the mailbox and totally upload to office 365 importing the errors too.
any advice.
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unrealone1Asked:
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Eoin OSullivanConsultantCommented:
Maybe try using a tool such as OLM to PST converter to get the mailbox out of Outlook
http://olmtopstconverterpro.com/

I recommended it on this EE article and it worked well for this other user
http://www.experts-exchange.com/OS/Apple_Operating_Systems/OS_X/Q_28687075.html

As Office 365 can handle PST imports it might be a transfer method

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