Having the exact same issue in our office. Office 365 E1 subscription with Macs running a mix of Mavericks and Yosemite and Outlook 2011 and Outlook for Mac v15. We have about 20 users and most of them are experiencing this problem, including a brand new user set up on Thursday (so the profile rebuild suggestion I've seen would be pointless). Hugely vexing problem that is causing us to rethink our use of Office 365. Clearly Mac support is not a priority for MSFT.
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