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.
Clearly the guys on the Exchange team have heard your complaints, as they have just release a new hybrid troubleshooting wizard. You can access this new tool at the link below
Disclaimer: This is a brand new tool, and has not been fully run through its paces yet. Please consider this to be a beta at this point.
Running this tool will log you into your Office 365 portal, then start a list of scripted checks. I have not personally had a chance to test the tool out much at this point. My personal Office 365 tenant is not current setup in hybrid mode. I’m going to start work on setting that up (again) and vetting this tool a bit more, but for some reasons my customers still expect me to work on their deployments so that might not happen as quickly as I would like.
Try it out, and let me know how it goes. If you do run into any problems, the team putting this tool would love to know about them. Reach out to me, and I’ll be happy to pass those comments along.