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Outlook 2011 not syncing

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I have posted 2 trouble tickets and gotten no response. Something happened in the last couple weeks as I am getting reports of:

1. Outlook not connecting

2. Outlook sending emails twice

3. Emails not going through or sitting in Outbox

4. Outlook dropping connection

5. Outlook requiring a send/recieve to get or send emails

 

Now granted these users are all Mac users and not very skilled but I have repaired databases, rebuilt databases, and reinstalled Office. Generally I can get these users working again but they are HATING The Cloud mail. What is going on? My PCs with Office 2013 have NONE of these issues...


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