I use Ansible to deploy Chocolatey packages on Windows Server 2016 machines (hosted on Amazon EC2). Yesterday, I re-created a brand new cluster for training purposes and I attempted to re-deploy my applications on it from scratch.
I’ve done this process countless times but yesterday it started to fail even though the playbooks had not changed in a while. After a fair amount of debugging, I found out that the error is caused by Chocolatey version 0.10.13.
Because the EC2 instances were created yesterday (24/03/2019), version 0.10.13 is the version that Ansible installed when it invoked the win_chocolatey command the 1st time around.
This isn’t something I’ve tested to prove it works so you would just have to try it and see how it goes. The alternative option is to use an internal repo and don’t add the latest Chocolatey version nupkg and source it from there.