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Reviewing through your description I would suggest submitting a case in your customer group here in the Jive Community so that the next available support engineer can collect logs and investigate further. When you submit the case, if you could please replicate the issue, note the time and provide the Microsoft logs from your machine (How to Find the Jive for Office and Outlook Logs ) to the case this will assist in the investigation.
We have the same problem, both in 30.3.5 and after regression to 30.2. We have also raised a case #397020.