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Now, am going to guess you configured the account by just entering the email address/password for the account which would default to IMAP. (the email account type is in the right hand column) If you're not sure, from within Outlook, go to File -> Account Settings -> Email tab #2 - How is this email configured where how = POP3, IMAP etc? #1 - You have an email account configured in Outlook 365 - correct?
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OK - let's go thru this in small steps to make things easier, Will leave the email portion of this to the end Haven't done this in a very long time but back in the day, always had a great experience with the tool as did everyone else that I was aware of who used it - never ran into a negative review but that doesn't mean it's the best or only one - just relaying personal experience. Diane has a list of 3rd party tools at the bottom of her article.
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May not be free but will save you all kinds of aggravation and time. In terms of the email data, personally would strongly suggest using a 3rd party conversion tool.
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If you have any questions about this process when you get to that point, don't hesitate to ask. Moving contact/calendar data is the simplest portion of this transition which requires the data exported from OE to a CSV file and then import those files in Outlook using the Outlook import wizard. With that in mind, one of the better articles on the topic is by Outlook MVP Diane Poremsky Only thing I mean by that is that it's not a one-step all-done process. First, be forewarned that there is nothing straight-forward about manually migrating everything from OE to a current version of Outlook.