Exchange 2013 Hybrid Configuration Wizard Fails

Several weeks ago I was working on a project where we were implement a hybrid environment with Office 365 by using Exchange 2013 as the hybrid servers for an existing Exchange 2010 environment. Adding Exchange 2013 went pretty smoothly overall and I thought the hybrid wizard would be the easy part.

When we ran the hybrid configuration wizard and selected the certificate, we got the following error:

The length of the property is too long

What a delightfully vague response. Well, after several days working with Office 365 tech support, the client was able to identify that the subject in the certificate was too long. The certificate was perfectly valid, but the hybrid configuration wizard was unable to handle the subject length.

The client had obtained an extended validation certificate that included a lot of additional information in the subject such as a long organization ID. After replacing the extended validation certificate with a standard certificate it completed without any problems.