Troubleshooting the Office 365 Hybrid Configuration Wizard

In this blog post I want to share some tips for identifying issues when running the Office 365 Hybrid Configuration Wizard (HCW), available here .

Specifically,

  1. Where to find the Hybrid Configuration Wizard logs
  2. How to identify network related issues

In my experience, network relates issues are the most common cause of HCW failures, and that is where this blog post will focus.   Most corporate networks have firewall and / or proxy restrictions in place.  There are very specific network requirements for connectivity to Office 365 as detailed here . read more

Outlook client can’t connect to Exchange 2016 – continually prompts for login credentials

Problem

I came across this issue while working on an Exchange Hybrid deployment.  During the testing phase, I successfully migrated mailboxes from Exchange 2010 to Exchange Online.  However, when I migrated a mailbox from Exchange 2010 to Exchange 2016, my Outlook client could not connect to its mailbox and would continually prompt for login credentials read more

Unable to run Office 365 / Exchange Hybrid Wizard – “Content was blocked because it was not signed by a valid security certificate”

Unable to run Office 365 / Exchange Hybrid Wizard – “Content was blocked because it was not signed by a valid security certificate”

Problem

From the Exchange Admin Center you run the Hybrid configuration setup

Hybrid1

You are prompted to login to Office 365

Hybrid2

You enter your credentials

Hybrid3

And then receive this message / warning

Hybrid4

You are unable to complete the Hybrid configuration

Solution

You can resolve this issue by installing the certificate as follows: read more

Can’t login to Office365 using Single Sign-On if UPN uses sub-domain

Scenario:

You have federated your domain with Office 365 to provide Single Sign-On for your users

Problem

Some or all of your users cannot sign into Office 365.  Users are presented with the following error:

SSO1

Looking closer at the description you see the following:

AADSTS50107: Requested federation realm object ‘http://subdomain.domain.com/adfs/services/trust/’ does not exist. read more