diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 053c53a..6d07d0c 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -287,6 +287,13 @@ jobs:
     name: Publish Chocolatey Package
     runs-on: windows-latest
     steps:
+      - name: Configure SSH for Git
+        run: |
+          mkdir -p ~/.ssh
+          echo "${{ secrets.RELEASE_BOT_SSH_KEY }}" > ~/.ssh/id_ed25519
+          chmod 600 ~/.ssh/id_ed25519
+          ssh-keyscan -H github.com >> ~/.ssh/known_hosts
+
       - name: Checkout repository
         uses: actions/checkout@v4
         with:
@@ -316,7 +323,13 @@ jobs:
 
       - name: Package and Publish package to Chocolatey
         run: |
-          mkdir ./deployment/chocolatey/tools
+          # Cleanup old package files
+          if (-not (Test-Path -Path './deployment/chocolatey/tools' -PathType Container)) {
+              New-Item -Path './deployment/chocolatey/tools' -ItemType Directory
+          }
+          rm -Force ./deployment/chocolatey/tools/chocolateyinstall.ps1
+          rm -Force ./deployment/chocolatey/managarr.nuspec
+
           # Run packaging script
           python "./deployment/chocolatey/packager.py" ${{ env.RELEASE_VERSION }} "./deployment/chocolatey/managarr.nuspec.template" "./deployment/chocolatey/managarr.nuspec" ${{ env.WINDOWS_SHA }}
           python "./deployment/chocolatey/packager.py" ${{ env.RELEASE_VERSION }} "./deployment/chocolatey/chocolateyinstall.ps1.template" "./deployment/chocolatey/tools/chocolateyinstall.ps1" ${{ env.WINDOWS_SHA }}
@@ -329,6 +342,14 @@ jobs:
           $version = $version -replace " ", "."
           choco push $version.nupkg -s https://push.chocolatey.org/ --api-key ${{ secrets.CHOCOLATEY_API_KEY }};
 
+          # Persist changes into repo
+          cd ../../
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          git add ./deployment/chocolatey/tools/chocolateyinstall.ps1 ./deployment/chocolatey/managarr.nuspec
+          git commit -m "chore: Update Chocolatey package for version ${{ env.RELEASE_VERSION }} [skip ci]"
+          git push origin main
+
   publish-docker-image:
     needs: [publish-github-release]
     name: Publishing Docker image to Docker Hub
diff --git a/deployment/chocolatey/packager.py b/deployment/packager.py
similarity index 100%
rename from deployment/chocolatey/packager.py
rename to deployment/packager.py