diff --git a/.github/workflows/pr-to-update-choco.yml b/.github/workflows/pr-to-update-choco.yml
new file mode 100644
index 0000000000..1f9403f4d6
--- /dev/null
+++ b/.github/workflows/pr-to-update-choco.yml
@@ -0,0 +1,125 @@
+name: PR for updating Chocolatey
+
+# This action will run after a tag starting with "v" is published
+# on:
+#   push:
+#     tags:
+#       - 'v*'
+#   workflow_dispatch:
+
+on:
+  push:
+    branches:
+      - automate-choco-workflow
+
+permissions:
+  contents: read
+
+jobs:
+  choco-update:
+    permissions:
+      contents: write # for Git to git push
+      pull-requests: write # for creating PRs
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout Headlamp
+        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        with:
+          token: ${{ secrets.KINVOLK_REPOS_TOKEN }}
+          # we need the full history for the git tag command, so fetch all the branches
+          fetch-depth: 0
+      - name: Configure Git
+        run: |
+          user=${{github.actor}}
+          if [ -z $user ]; then
+            user=vyncent-t
+          fi
+          git config --global user.name "$user"
+          git config --global user.email "$user@users.noreply.github.com"
+      # Set up Node.js environment, pay attention to the version
+      # Some features might not be available in older versions
+      - name: Create node.js environment
+        uses: actions/setup-node@60edb5dd545a775178f52524783378180af0d1f8 # v4.0.2
+        with:
+          node-version: '21'
+      # Install the app dependencies for the choco script
+      - name: Install app dependencies
+        run: |
+          cd $GITHUB_WORKSPACE/app
+          npm ci
+      # We set the latest tag as an environment variable before we use it in the next steps
+      # note that we have to echo the variable to the environment file to make it available in the next steps
+      - name: Set latest tag
+        run: |
+          echo "Setting latest tag"
+          latestTag=$(git tag --list --sort=version:refname 'v*' | tail -1)
+          # Remove the 'v' from the tag
+          latestTag=${latestTag#v}
+          echo "LATEST_HEADLAMP_TAG=$latestTag" >> $GITHUB_ENV
+          echo $latestTag
+      - name: Download checksum
+        run: |
+          echo "Downloading checksum"
+          cd $GITHUB_WORKSPACE/app/windows/chocolatey
+          curl -L -O "https://github.com/headlamp-k8s/headlamp/releases/download/v$LATEST_HEADLAMP_TAG/checksums.txt"
+          echo "Checksum downloaded"
+          if [ -f checksums.txt ]; then
+            echo "Checksum file exists"
+          else
+            echo "Checksum file does not exist"
+            exit 1
+          fi
+      - name: Set hash and checksum
+        run: |
+          echo "Setting hash and checksum"
+          cd $GITHUB_WORKSPACE/app/windows/chocolatey
+          ls
+          read -r hash win_file_name <<< $(grep 'win-x64' ./checksums.txt)
+          echo "Hash: $hash"
+          echo "Win file name: $win_file_name"
+          echo "WIN_FILE_NAME=$win_file_name" >> $GITHUB_ENV
+          echo "WIN_FILE_HASH=$hash" >> $GITHUB_ENV
+      # Run the choco script
+      - name: Create nuget package
+        run: |
+          echo "Running choco script"
+          echo "Repository: ${{ github.repository }}"
+          echo "Workspace: ${GITHUB_WORKSPACE}"
+          echo $GITHUB_WORKSPACE
+          pwd
+          echo "LATEST_HEADLAMP_TAG=$LATEST_HEADLAMP_TAG"
+          echo "WIN_FILE_HASH=$WIN_FILE_HASH"
+          echo "creating nuget pkgs"
+          cd $GITHUB_WORKSPACE/app/windows/chocolatey
+          ./choco-bump.sh $LATEST_HEADLAMP_TAG $WIN_FILE_HASH
+          echo "Script finished"
+          echo "Checksum file still exists"
+          ls
+          echo "Removing checksums.txt"
+          rm $GITHUB_WORKSPACE/app/windows/chocolatey/checksums.txt
+          ls
+          echo "Checksum file removed"
+      # REFACTOR FOR CUSTOM NUGET REPO LATER IF NEEDED
+      - name: Create PR branch and push
+        run: |
+          user=${{github.actor}}
+          if [ -z $user ]; then
+            user=vyncent-t
+          fi
+          echo "Creating PR branch"
+          echo "Repository: ${{ github.repository }}"
+          echo "Workspace: ${GITHUB_WORKSPACE}"
+          pwd
+          ls
+          echo echo "https://github.com/headlamp-k8s/headlamp/pull/new/WIP0-choco-update-$LATEST_HEADLAMP_TAG"
+          git checkout -b "choco-update-$LATEST_HEADLAMP_TAG"
+          git add .
+          git commit -s -m "chocolatey: Bump Headlamp version to $LATEST_HEADLAMP_TAG"
+          git push origin "choco-update-$LATEST_HEADLAMP_TAG"
+          gh pr create \
+            --title "chocolatey: Bump Headlamp version to $LATEST_HEADLAMP_TAG" \
+            --base main \
+            --assignee $user \
+            --body "This PR updates the chocolatey package to the latest version of Headlamp" \
+        env:
+          GITHUB_TOKEN: ${{ secrets.KINVOLK_REPOS_TOKEN }}
diff --git a/app/windows/chocolatey/checksums.txt b/app/windows/chocolatey/checksums.txt
new file mode 100644
index 0000000000..c1e50a7fe3
--- /dev/null
+++ b/app/windows/chocolatey/checksums.txt
@@ -0,0 +1,10 @@
+4a926c3f9175fca2f71bd777db33b0a9b272cd88e980f6d9ca3422ef99a0035e  Headlamp-0.27.0-linux-arm64.AppImage
+cbaecfba70966938d6d9c6883b267e8c7e5f33c8b823a2d225d78a39f51921f6  Headlamp-0.27.0-linux-arm64.tar.gz
+2d369e7f9bb70676b7e48e2d8aafe667fc9748f7a4189074e8d7ad5e7ed01251  Headlamp-0.27.0-linux-armv7l.AppImage
+81e941a6b9f74b9f5abde787ff4a3d6022e5a6a003ce5a00a41ea7e0b85290f3  Headlamp-0.27.0-linux-armv7l.tar.gz
+0e12d342cd1cc491173d1cc0776049ad0cacf1f3972f87c7704d5a15031fba21  Headlamp-0.27.0-linux-x64.AppImage
+11955d1b81d3ce45ae13d03541904ab07222b0ebf84d077582102b454b9d2255  Headlamp-0.27.0-linux-x64.tar.gz
+d4ed9d1fe4313053ac5be577e12fdddbdc8495bef415147b518e81cdd3644249  Headlamp-0.27.0-mac-arm64.dmg
+a5e8b2821890012e2c5ef0695863a5d83bbbc66d64bc6a057a036fac6f2ad9c0  Headlamp-0.27.0-mac-x64.dmg
+b94dec3f29b0024a694e140ec0a343e8143d147f352fde095eda4908e141035d  Headlamp-0.27.0-win-x64.exe
+6582c5500e3e76092c1d729596ebd13431c6089f71df604e28c83525552083b3  headlamp_0.27.0-1_amd64.deb