Error – “Updating hybrid configuration failed with error ‘Subtask Configure execution failed: Configure Mail Flow”

When  you try to run the  Hybrid Configuration wizard you get the following error:

Error –  “Updating hybrid configuration failed with error ‘Subtask Configure execution failed: Configure Mail Flow”

If you are using wildcard certificate in your default website in IIS  ,*.domain.com is not a valid FQDN for a send connector in Exchange sp2 . There two ways to solve this issue :

1. Install exchange SP2 rollup 1 – http://www.microsoft.com/download/en/details.aspx?id=28809

2.If you dont want to  install the update, i  found a workaround in this  a grate article

http://clintboessen.blogspot.com/2011/12/wild-card-certificates-and-hybrid.html

Basically, what you need to do in order to complete the Hybrid Configuration Wizard is to use a free  digital certificate from http://www.freessl.com/ complete the wizard and then replace it back to your wildcard certificate.

About Idit Bnaya

Sr. Cloud Solution Architect at Microsoft, I’m passionate about helping customers succeed by building secure, scalable, and innovative cloud solutions – with a strong focus on AI, DevOps practices, and end-to-end security. With a proven track record in the IT and services industry, I serve as a trusted advisor, partnering closely with organizations to guide them through digital transformation and maximize the value of their cloud investments. My role combines technical leadership with project ownership – from designing modern architectures to leading cross-functional implementations that drive real business outcomes. I also manage and empower strategic partners, working hand-in-hand with them to ensure project success and deliver measurable business impact for customers.
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2 Responses to Error – “Updating hybrid configuration failed with error ‘Subtask Configure execution failed: Configure Mail Flow”

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