Anyone who has ever done an Exchange Online hybrid deployment can tell you that process can be frustrating. Before the Hybrid Configuration Wizard the process was long and complicated with too many steps and too many places to make a small mistake. With the advent of the HCW the process became much more of a “black box” where the guy doing the deployment really didn’t know what configuration changes were being made, so misconfigurations became very hard to troubleshoot. Add on top of all that the fact that you, and the person doing the deployment really have no control or visibility into the Microsoft side of thing, and a hybrid deployment quickly turns into a difficult task.

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