As a side note, the same issue persist on Windows with HP current gen EliteBook and Office. Everytime I undock the notebook, MS Outlook gets disconnected and it simply refuses to reconnect. The only option is to close Outlook and open it again - but waiting 30s between closing and starting again otherwise some locks on the PST file are still in place and Outlook would hang on start forever. The only way to fix it then, is by a Windows reboot. That they killed the QA department was the dumbest idea ever, now things are so buggy.