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By default, actions/checkout configures GITHUB_TOKEN for authentication. The problem is that events caused by GITHUB_TOKEN cannot trigger new workflows as described in Using the GITHUB_TOKEN in a workflow:

When you use the repository’s GITHUB_TOKEN to perform tasks on behalf of the GitHub Actions app, events triggered by the GITHUB_TOKEN will not create a new workflow run.

If you want the push to create new workflow runs you need to use a PAT instead. After adding it as a secret you can do something like this to use it instead of GITHUB_TOKEN:

- uses: actions/checkout@v2
  with:
    token: ${{ secrets.PAT }}

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@sebthom
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@I-Want-ToBelieve
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