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Back in the day (~10 years ago?) when the company I worked for was looking at replacing our internal custom provisioning and desired state configuration tooling

Back in the day (~10 years ago?) when the company I worked for was looking at replacing our internal custom provisioning and desired state configuration tooling it was Ansible that won out. We were running a mixed fleet of Windows and Linux hosts - the company was an ISP and shared hoster. At that point in time both Puppet and Chef needed agents to be installed on your servers and we really didn't want to have to manage another background service running on hundreds to thousands of boxes. Ansible didn't have this requirement. Also Windows support was pretty sketchy on Chef and Puppet back then, to the point of being almost studiously ignored, Ansible provided remote PowerShell support. And that was primarily the deciding factor.

twic 5y ago
I used Puppet around 2012. I remember looking at Ansible, and immediately seeing that its agentless, SSH-based approach was highly preferable. But every time i discussed it with the devops experts in and contracted to our company, they assured me that agentless was terrible, and had too many disadvantages, and couldn't scale. And yet, here we are. Puppet grew an agentless mode, and then lost anyway. My former company's deep investment in integrating Puppet and MCollective into our infrastructure tooling must look increasingly like a millstone. Oh well, it was all interesting to work on.