On Mon, 4 May 2020 11:55:19 -0700 (PDT)
Justin Nelson <[email protected]> wrote:

> ... When I run my playbook I can only seem to get one of my two hosts ...
> 
> - name: Update File
>   hosts:
>     - test_group
>   connection: local
>
> [...]
>
> [test_group]
> host1
> host2
>
> [...]
>
> What am I missing to make this work for both hosts?

Remove "connection: local". See "local – execute on controller"
https://docs.ansible.com/ansible/latest/plugins/connection/local.html#local-execute-on-controller

  "... allows ansible to execute tasks on the Ansible ‘controller’ instead of
  on a remote host."

HTH,

        -vlado

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