VMware Cloud Foundation – Failed to generate certificate for {fqdn} due to: Microsoft CA signing request error

This week I spun up my home lab to prepare it for something I’m working on and noticed that I’d never applied signed certificates to the deployed components so before starting on anything new I decided to address this first. What I thought would take 30 mins turned into a little more effort than planned.

Generating the CSRs went fine but as soon as I tried to generate the certificate files using my integrated Microsft CA server I was presented with the following error:

As you can see the error information provided is not very helpful, I decided to double check all of my Microsoft Certificate Authority configuration using the Prepare Your Microsoft Certificate Authority to Enable SDDC Manger to Manage Certificates documentation contained within the VMware Cloud Foundation Administration Guide.

It didn’t take long and sure enough I found that I had somehow missed enabling basic authentication, so I applied Step 3 from Configure the Microsoft Certificate Authority for Basic Authentication section. Then attempted to perform the certificate generation process and low and behold it proceeded without any issues.

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