diff --git a/.github/workflows/test-chocolatey-deploy.yml b/.github/workflows/test-chocolatey-deploy.yml
new file mode 100644
index 0000000..3341eac
--- /dev/null
+++ b/.github/workflows/test-chocolatey-deploy.yml
@@ -0,0 +1,56 @@
+name: Test release Managarr to Chocolatey
+
+permissions:
+  pull-requests: write
+  contents: write
+
+on:
+  workflow_dispatch:
+
+jobs:
+  publish-chocolatey-package:
+    needs: [publish-github-release]
+    name: Publish Chocolatey Package
+    runs-on: windows-latest
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v4
+        with:
+          fetch-depth: 1
+
+      - name: Get release artifacts
+        uses: actions/download-artifact@v4.1.7
+        with:
+          name: artifacts
+          path: artifacts
+
+      - name: Set release assets and version
+        shell: pwsh
+        run: |
+          # Read the first column from the SHA256 file
+          $windows_sha = Get-Content ./artifacts/managarr-windows.sha256 | ForEach-Object { $_.Split(' ')[0] }
+          Add-Content -Path $env:GITHUB_ENV -Value "WINDOWS_SHA=$windows_sha"
+
+          # Read the release version from the release-version file
+          $release_version = Get-Content ./artifacts/release-version
+          Add-Content -Path $env:GITHUB_ENV -Value "RELEASE_VERSION=$release_version"
+
+      - name: Validate release environment variables
+        run: |
+          echo "Release SHA windows: ${{ env.WINDOWS_SHA }}"
+          echo "Release version: ${{ env.RELEASE_VERSION }}"
+
+      - name: Package and Publish package to Chocolatey
+        run: |
+          mkdir ./deployment/chocolatey/tools
+          # 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 }}
+
+          # Publish to Chocolatey
+          cd ./deployment/chocolatey
+          choco pack
+          echo y | choco install managarr -dv -s .
+          $version = managarr --version
+          $version = $version -replace " ", "."
+          choco push $version.nupkg -s https://push.chocolatey.org/ --api-key ${{ secrets.CHOCOLATEY_API_KEY }};
diff --git a/deployment/chocolatey/chocolateyinstall.ps1.template b/deployment/chocolatey/chocolateyinstall.ps1.template
new file mode 100644
index 0000000..e70133a
--- /dev/null
+++ b/deployment/chocolatey/chocolateyinstall.ps1.template
@@ -0,0 +1,20 @@
+$ErrorActionPreference = 'Stop';
+
+$PackageName = 'kdash'
+$toolsDir    = "$(Split-Path -parent $MyInvocation.MyCommand.Definition)"
+$url64       = 'https://github.com/Dark-Alex-17/managarr/releases/download/v$version/managarr-windows.tar.gz'
+$checksum64  = '$hash_64'
+
+$packageArgs = @{
+  packageName   = $packageName
+  softwareName  = $packageName
+  unzipLocation = $toolsDir
+  fileType      = 'exe'
+  url           = $url64
+  checksum      = $checksum64
+  checksumType  = 'sha256'
+
+}
+Install-ChocolateyZipPackage @packageArgs
+$File = Get-ChildItem -File -Path $env:ChocolateyInstall\lib\$packageName\tools\ -Filter *.tar
+Get-ChocolateyUnzip -fileFullPath $File.FullName -destination $env:ChocolateyInstall\lib\$packageName\tools\
diff --git a/deployment/chocolatey/managarr.nuspec.template b/deployment/chocolatey/managarr.nuspec.template
new file mode 100644
index 0000000..a421a22
--- /dev/null
+++ b/deployment/chocolatey/managarr.nuspec.template
@@ -0,0 +1,53 @@
+<?xml version="1.0" encoding="utf-8"?>
+<!-- Read this before creating packages: https://chocolatey.org/docs/create-packages -->
+<!-- It is especially important to read the above link to understand additional requirements when publishing packages to the community feed aka dot org (https://chocolatey.org/packages). -->
+
+<!-- Test your packages in a test environment: https://github.com/chocolatey/chocolatey-test-environment -->
+
+<!--
+This is a nuspec. It mostly adheres to https://docs.nuget.org/create/Nuspec-Reference. Chocolatey uses a special version of NuGet.Core that allows us to do more than was initially possible. As such there are certain things to be aware of:
+
+* the package xmlns schema url may cause issues with nuget.exe
+* Any of the following elements can ONLY be used by choco tools - projectSourceUrl, docsUrl, mailingListUrl, bugTrackerUrl, packageSourceUrl, provides, conflicts, replaces 
+* nuget.exe can still install packages with those elements but they are ignored. Any authoring tools or commands will error on those elements 
+-->
+
+<!-- You can embed software files directly into packages, as long as you are not bound by distribution rights. -->
+<!-- * If you are an organization making private packages, you probably have no issues here -->
+<!-- * If you are releasing to the community feed, you need to consider distribution rights. -->
+<!-- Do not remove this test for UTF-8: if “Ω” doesn’t appear as greek uppercase omega letter enclosed in quotation marks, you should use an editor that supports UTF-8, not this one. -->
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <!-- == PACKAGE SPECIFIC SECTION == -->
+    <id>managarr</id>
+    <version>$version</version>
+
+    <!-- == SOFTWARE SPECIFIC SECTION == -->
+    <!-- This section is about the software itself -->
+    <title>Managarr</title>
+    <authors>Alex Clarke</authors>
+    <projectUrl>https://github.com/Dark-Alex-17/managarr</projectUrl>
+    <licenseUrl>https://github.com/Dark-Alex-17/managarr/blob/main/LICENSE</licenseUrl>
+    <requireLicenseAcceptance>true</requireLicenseAcceptance>
+    <projectSourceUrl>https://github.com/Dark-Alex-17/managarr</projectSourceUrl>
+    <docsUrl>https://github.com/Dark-Alex-17/managarr/blob/main/README.md</docsUrl>
+    <bugTrackerUrl>https://github.com/Dark-Alex-17/managarr/issues</bugTrackerUrl>
+    <tags>cli cross-platform terminal servarr tui sonarr radarr rust</tags>
+    <summary>A TUI and CLI for managing *arr servers.</summary>
+    <description>
+    A TUI and CLI for managing *arr servers. Build with love in Rust!
+
+    **Usage**
+    To use, run `managarr` in a terminal.
+    
+    For more [documentation and usage](https://github.com/Dark-Alex-17/managarr/blob/main/README.md), see the [official repo](https://github.com/Dark-Alex-17/managarr).
+    
+    </description>
+    <releaseNotes>https://github.com/Dark-Alex-17/managarr/releases/tag/v$version/</releaseNotes>
+  </metadata>
+  <files>
+    <!-- this section controls what actually gets packaged into the Chocolatey package -->
+    <file src="tools\**" target="tools" />
+    <!--Building from Linux? You may need this instead: <file src="tools/**" target="tools" />-->
+  </files>
+</package>
diff --git a/deployment/chocolatey/packager.py b/deployment/chocolatey/packager.py
new file mode 100644
index 0000000..e2d1837
--- /dev/null
+++ b/deployment/chocolatey/packager.py
@@ -0,0 +1,27 @@
+import hashlib
+import sys
+from string import Template
+
+args = sys.argv
+version = args[1].replace("v", "")
+template_file_path = args[2]
+generated_file_path = args[3]
+
+# Deployment files
+hash_64 = args[4].strip()
+
+print("Generating formula")
+print("     VERSION: %s" % version)
+print("     TEMPLATE PATH: %s" % template_file_path)
+print("     SAVING AT: %s" % generated_file_path)
+print("     HASH: %s" % hash_64)
+
+with open(template_file_path, "r") as template_file:
+    template = Template(template_file.read())
+    substitute = template.safe_substitute(version=version, hash_64=hash_64)
+    print("\n================== Generated package file ==================\n")
+    print(substitute)
+    print("\n============================================================\n")
+
+    with open(generated_file_path, "w") as generated_file:
+        generated_file.write(substitute)
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