feat: implement package manager support for Windows and macOS, including Chocolatey and Homebrew configurations

DEVELOPMENT_PLAN.md

@@ -1197,6 +1197,27 @@ February 2026
 
 ---
 
+### Decision: Package Manager Support (Phase 5)
+
+**Options:**
+1. Only direct downloads
+2. Single package manager (Chocolatey OR Homebrew)
+3. Multiple package managers (Chocolatey AND Homebrew) with custom taps
+
+**Decision**: **Multi-channel distribution via package managers**
+- **Windows**: Chocolatey community repository or internal NuGet
+- **macOS**: Custom Homebrew tap on Forgejo (HIM-public/homebrew-webdrop-bridge)
+- **Fallback**: Direct wget downloads + built-in auto-update system
+- **Implementation**: Supports both official repos and internal/private hosting
+
+**Implementation Details:**
+- Chocolatey: `build/chocolatey/` with .nuspec manifest
+- Homebrew: `build/homebrew/` with Ruby formula
+- Auto-download checksums from Forgejo releases
+- Documentation in `docs/PACKAGE_MANAGER_SUPPORT.md`
+
+---
+
 ### Decision: Telemetry
 
 **Options:**
@@ -1255,23 +1276,24 @@ Phase 4 Complete - Professional Features & Auto-Update system fully implemented.
    - Cross-platform testing on Windows 10/11, macOS 12-14
    - Security hardening and final audit
    - Performance optimization (drag latency < 50ms)
+   - **Package Manager Setup** (NEW):
+     - Chocolatey packaging and publishing workflow
+     - Homebrew tap creation for custom distribution
+     - Documentation for package manager support
 
 2. **Testing & Validation**:
    - Run full test suite on both platforms
    - User acceptance testing with real-world scenarios
+   - Package manager installation testing
    - Documentation review and finalization
 
 3. **Finalization**:
    - Announce stable release v1.0.0
    - Publish installers to Forgejo Packages
+   - Publish to Chocolatey (community or internal)
+   - Create and publish Homebrew tap
    - Enable auto-update system for users
 
-3. **Finalization**:
-   - Code signing for Windows MSI (optional)
-   - Apple notarization for macOS DMG (future)
-   - Create stable v1.0.0 release
-   - Publish to Forgejo Packages
-
 ---
 
 ## Document Control

QUICKSTART.md

@@ -110,7 +110,40 @@ tox
 
 ### Installing from Release (wget)
 
-Download pre-built installers from Forgejo releases using **wget** (useful for enterprise deployments, automated scripts, or initial setup before the built-in update mechanism):
+Download pre-built installers from Forgejo releases using **wget**, **package managers**, or **automated scripts** (useful for enterprise deployments, automated scripts, or initial setup before the built-in update mechanism):
+
+#### Package Manager (Easiest)
+
+**Windows (Chocolatey)**
+
+```powershell
+# Install
+choco install webdrop-bridge
+
+# Upgrade to latest
+choco upgrade webdrop-bridge
+
+# Uninstall
+choco uninstall webdrop-bridge
+```
+
+**macOS (Homebrew with custom tap)**
+
+```bash
+# Add tap (one-time setup)
+brew tap HIM-public/webdrop-bridge https://git.him-tools.de/HIM-public/homebrew-webdrop-bridge.git
+
+# Install
+brew install webdrop-bridge
+
+# Upgrade
+brew upgrade webdrop-bridge
+
+# Uninstall
+brew uninstall webdrop-bridge
+```
+
+For more package manager details and internal hosting options, see [docs/PACKAGE_MANAGER_SUPPORT.md](../docs/PACKAGE_MANAGER_SUPPORT.md)
 
 #### Simplest: Direct wget (if you know the version)
 

README.md

@@ -40,7 +40,22 @@ WebDrop Bridge embeds a web application in a Qt container with full filesystem a
 
 ### Installation from Pre-Built Release (Recommended)
 
-**Simplest Method: Direct wget (if you know the version)**
+**Option 1: Package Manager (Recommended for most users)**
+
+```powershell
+# Windows - Chocolatey
+choco install webdrop-bridge
+choco upgrade webdrop-bridge  # Update when new version available
+```
+
+```bash
+# macOS - Homebrew (with custom tap)
+brew tap HIM-public/webdrop-bridge https://git.him-tools.de/HIM-public/homebrew-webdrop-bridge.git
+brew install webdrop-bridge
+brew upgrade webdrop-bridge  # Update to latest version
+```
+
+**Option 2: Direct wget (if you know the version)**
 
 ```bash
 # Replace VERSION with release tag (e.g., v0.8.0)
@@ -50,7 +65,7 @@ wget https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/VERSIO
 wget https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/v0.8.0/WebDropBridge_Setup.msi
 ```
 
-**Alternative: Automated script (auto-detects platform)**
+**Option 3: Automated script (auto-detects platform)**
 
 ```bash
 # Windows (PowerShell)
@@ -60,7 +75,7 @@ wget https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/v0.8.0
 ./build/scripts/download_release.sh
 ```
 
-For more installation options and details, see [QUICKSTART.md](QUICKSTART.md#installing-from-release-wget)
+For more installation options and details, see [QUICKSTART.md](QUICKSTART.md#installing-from-release-wget) and [PACKAGE_MANAGER_SUPPORT.md](docs/PACKAGE_MANAGER_SUPPORT.md)
 
 ### Installation from Source
 

build/chocolatey/tools/chocolateyInstall.ps1

@@ -0,0 +1,47 @@
+$ErrorActionPreference = 'Stop'
+
+$PackageName = 'webdrop-bridge'
+$Version = '0.8.0'
+$Url = "https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/v$Version/WebDropBridge_Setup.msi"
+$Checksum = '' # Update with actual SHA256 checksum from release
+$ChecksumType = 'sha256'
+
+# Create temporary directory for download
+$TempDir = Join-Path $env:TEMP "webdrop-bridge-$Version"
+New-Item -ItemType Directory -Path $TempDir -Force | Out-Null
+
+try {
+    # Download MSI installer
+    Write-Host "Downloading WebDropBridge $Version MSI installer..."
+    $InstallerPath = Join-Path $TempDir "WebDropBridge_Setup.msi"
+    
+    Get-ChocolateyWebFile -PackageName $PackageName `
+                          -FileFullPath $InstallerPath `
+                          -Url $Url `
+                          -Checksum $Checksum `
+                          -ChecksumType $ChecksumType
+
+    # Install MSI
+    Write-Host "Installing WebDropBridge..."
+    $InstallArgs = @(
+        '/i'
+        "`"$InstallerPath`""
+        '/quiet'  # Silent installation
+        '/norestart'  # Don't restart immediately
+    )
+    
+    Invoke-ChocolateyInstall -PackageName $PackageName `
+                             -File 'msiexec.exe' `
+                             -FileArgs $InstallArgs `
+                             -ValidExitCodes @(0, 3010)  # 0=success, 3010=restart needed
+
+    Write-Host "WebDropBridge installed successfully"
+} catch {
+    Write-Error "Installation failed: $_"
+    exit 1
+} finally {
+    # Cleanup
+    if (Test-Path $TempDir) {
+        Remove-Item $TempDir -Recurse -Force -ErrorAction SilentlyContinue
+    }
+}

build/chocolatey/tools/chocolateyUninstall.ps1

@@ -0,0 +1,38 @@
+$ErrorActionPreference = 'Stop'
+
+$PackageName = 'webdrop-bridge'
+
+try {
+    # Find installed version
+    $UninstallPath = Get-ChildItem HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall |
+        Where-Object { $_.GetValue('DisplayName') -like '*WebDropBridge*' } |
+        Select-Object -First 1
+
+    if ($UninstallPath) {
+        $UninstallString = $UninstallPath.GetValue('UninstallString')
+        
+        # Extract MSI Product ID from uninstall string
+        if ($UninstallString -match '{[A-F0-9-]+}') {
+            $ProductId = $matches[0]
+            
+            Write-Host "Uninstalling WebDropBridge (Product ID: $ProductId)..."
+            
+            $UninstallArgs = @(
+                '/x'
+                $ProductId
+                '/quiet'
+                '/norestart'
+            )
+            
+            & 'msiexec.exe' @UninstallArgs
+            
+            Write-Host "WebDropBridge uninstalled successfully"
+        } else {
+            Write-Warning "Could not extract Product ID from uninstall string"
+        }
+    } else {
+        Write-Warning "WebDropBridge is not installed"
+    }
+} catch {
+    Write-Error "Uninstall failed: $_"
+}

build/chocolatey/webdrop-bridge.nuspec

@@ -0,0 +1,28 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <id>webdrop-bridge</id>
+    <version>0.8.0</version>
+    <packageSourceUrl>https://git.him-tools.de/HIM-public/webdrop-bridge</packageSourceUrl>
+    <owners>HIM-public</owners>
+    <title>WebDrop Bridge</title>
+    <authors>HIM-public</authors>
+    <licenseUrl>https://git.him-tools.de/HIM-public/webdrop-bridge/blob/main/LICENSE</licenseUrl>
+    <projectUrl>https://git.him-tools.de/HIM-public/webdrop-bridge</projectUrl>
+    <bugTrackerUrl>https://git.him-tools.de/HIM-public/webdrop-bridge/issues</bugTrackerUrl>
+    <description>
+Professional Qt-based desktop application for intelligent drag-and-drop file handling between web applications and desktop clients (InDesign, Word, Notepad++, etc.)
+
+Converts text-based drag-and-drop operations from embedded web applications into native file operations recognized by professional desktop applications.
+    </description>
+    <summary>Intelligent drag-and-drop file bridge for web to desktop applications</summary>
+    <releaseNotes>https://git.him-tools.de/HIM-public/webdrop-bridge/releases/tag/v0.8.0</releaseNotes>
+    <tags>drag-drop file-transfer qt pyside6 desktop automation</tags>
+    <dependencies>
+      <dependency id="chocolatey" version="0.10.8" />
+    </dependencies>
+  </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>

build/homebrew/webdrop-bridge.rb

@@ -0,0 +1,48 @@
+class WebdropBridge < Formula
+  desc "Intelligent drag-and-drop file bridge for web to desktop applications"
+  homepage "https://git.him-tools.de/HIM-public/webdrop-bridge"
+  version "0.8.0"
+  
+  # ARM64 (Apple Silicon)
+  on_arm do
+    url "https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/v0.8.0/WebDropBridge_Setup.dmg"
+    sha256 "" # Update with actual checksum
+  end
+  
+  # Intel x86_64
+  on_intel do
+    url "https://git.him-tools.de/HIM-public/webdrop-bridge/releases/download/v0.8.0/WebDropBridge_Setup.dmg"
+    sha256 "" # Update with actual checksum (may be same as ARM64 if universal binary)
+  end
+  
+  license "MIT"
+  
+  livecheck do
+    url "https://git.him-tools.de/api/v1/repos/HIM-public/webdrop-bridge/releases/latest"
+    strategy :json do |json|
+      json["tag_name"]&.strip&.sub(/^v/, "")
+    end
+  end
+  
+  app "WebDropBridge.app"
+  
+  post_install do
+    # Create user defaults directory if needed
+    system "mkdir", "-p", "#{Dir.home}/.webdrop-bridge"
+  end
+  
+  def caveats
+    <<~EOS
+      WebDropBridge has been installed.
+      
+      Configuration files are stored in: ~/.webdrop-bridge/
+      Logs are written to: ~/.webdrop-bridge/logs/
+      
+      To start the application:
+      - Open Applications > WebDropBridge
+      - Or run: open /Applications/WebDropBridge.app
+      
+      For documentation: https://git.him-tools.de/HIM-public/webdrop-bridge
+    EOS
+  end
+end

build/package-managers/README.md

@@ -0,0 +1,126 @@
+# Package Manager Distributions
+
+This directory contains package manager configurations for distributing WebDropBridge across different platforms.
+
+## Directory Structure
+
+```
+build/
+├── chocolatey/                 # Windows - Chocolatey/NuGet package
+│   ├── webdrop-bridge.nuspec   # Package manifest
+│   └── tools/
+│       ├── chocolateyInstall.ps1   # Installation script
+│       └── chocolateyUninstall.ps1 # Uninstallation script
+│
+└── homebrew/                   # macOS - Homebrew formula
+    └── webdrop-bridge.rb       # Homebrew formula
+```
+
+## Quick Start
+
+### Chocolatey Package (Windows)
+
+1. **Build MSI installer**:
+   ```bash
+   python build/scripts/build_windows.py --msi
+   ```
+
+2. **Get SHA256 checksum**:
+   ```powershell
+   certutil -hashfile build/dist/windows/WebDropBridge_Setup.msi SHA256
+   ```
+
+3. **Update package files**:
+   - `build/chocolatey/webdrop-bridge.nuspec` - update `<version>`
+   - `build/chocolatey/tools/chocolateyInstall.ps1` - update `$Version` and `$Checksum`
+
+4. **Package it** (requires Chocolatey CLI):
+   ```powershell
+   cd build/chocolatey
+   choco pack webdrop-bridge.nuspec
+   ```
+
+5. **Publish** (requires Chocolatey API key):
+   ```powershell
+   choco push webdrop-bridge.0.8.0.nupkg --api-key YOUR_KEY
+   ```
+
+### Homebrew Formula (macOS)
+
+1. **Build DMG installer**:
+   ```bash
+   bash build/scripts/build_macos.sh
+   ```
+
+2. **Get SHA256 checksum**:
+   ```bash
+   shasum -a 256 build/dist/macos/WebDropBridge_Setup.dmg
+   ```
+
+3. **Update formula**:
+   - `build/homebrew/webdrop-bridge.rb` - update `version` and `sha256`
+
+4. **Test locally**:
+   ```bash
+   brew audit --formula build/homebrew/webdrop-bridge.rb
+   brew install build/homebrew/webdrop-bridge.rb
+   ```
+
+5. **Publish** (create Forgejo tap or submit to official Homebrew):
+   - Option A: Create `homebrew-webdrop-bridge` tap on Forgejo
+   - Option B: Submit to `homebrew/casks` on GitHub
+
+## Publishing Strategy
+
+### Recommended Approach for HIM
+
+1. **Chocolatey**:
+   - Host in internal Artifactory/Azure Artifacts NuGet repository
+   - OR submit to Chocolatey community (chocolatey.org)
+   - Users: `choco install webdrop-bridge`
+
+2. **Homebrew**:
+   - Create custom tap: `HIM-public/homebrew-webdrop-bridge` on Forgejo
+   - Users add tap: `brew tap HIM-public/webdrop-bridge https://git.him-tools.de/...`
+   - Users: `brew install webdrop-bridge`
+
+3. **Fallback**:
+   - Direct wget/downloads from Forgejo releases
+   - Built-in auto-update system in app
+
+## Release Checklist
+
+When releasing version X.Y.Z:
+
+- [ ] Build Windows MSI: `python build/scripts/build_windows.py --msi`
+- [ ] Build macOS DMG: `bash build/scripts/build_macos.sh`
+- [ ] Calculate checksums (certutil / shasum)
+- [ ] Create Forgejo release with installers
+- [ ] Update `build/chocolatey/webdrop-bridge.nuspec` version
+- [ ] Update `build/chocolatey/tools/chocolateyInstall.ps1` version & checksum
+- [ ] Update `build/homebrew/webdrop-bridge.rb` version & checksum
+- [ ] Test Chocolatey package locally
+- [ ] Test Homebrew formula locally
+- [ ] Publish to package managers
+
+## User Installation Commands
+
+After publishing:
+
+```powershell
+# Windows
+choco install webdrop-bridge
+```
+
+```bash
+# macOS
+brew tap HIM-public/webdrop-bridge https://git.him-tools.de/HIM-public/homebrew-webdrop-bridge.git
+brew install webdrop-bridge
+```
+
+## References
+
+- [Full Documentation](../../docs/PACKAGE_MANAGER_SUPPORT.md)
+- [Chocolatey Docs](https://docs.chocolatey.org/)
+- [Homebrew Docs](https://docs.brew.sh/)
+- [Forgejo API](https://docs.gitea.com/api/1.22/)

docs/PACKAGE_MANAGER_SUPPORT.md

@@ -0,0 +1,391 @@
+# Package Manager Support for WebDropBridge
+
+This document explains how to build and publish WebDropBridge to package managers like Chocolatey (Windows) and Homebrew (macOS).
+
+## Overview
+
+WebDropBridge supports installation via package managers, making it easier for users to install, update, and manage the application.
+
+| Package Manager | OS | Status | Directory |
+|-----------------|-----|--------|-----------|
+| **Chocolatey** | Windows | Supported | `build/chocolatey/` |
+| **Homebrew** | macOS | Supported | `build/homebrew/` |
+| **Winget** | Windows | Optional | Future |
+
+## Quick Start: Simplest Approach (Direct Distribution)
+
+**No infrastructure or accounts needed** - just build once and share:
+
+```powershell
+# 1. Build the Chocolatey package
+cd build/chocolatey
+python ../../build/scripts/build_windows.py --msi
+certutil -hashfile "../../build/dist/windows/WebDropBridge_Setup.msi" SHA256
+# Update checksum in tools/chocolateyInstall.ps1
+choco pack webdrop-bridge.nuspec
+
+# 2. Share webdrop-bridge.0.8.0.nupkg
+#    File share: \\server\packages\
+#    USB drive, email, Forgejo releases, etc.
+
+# 3. Users install it
+#    choco install webdrop-bridge.0.8.0.nupkg -s "\\server\packages"
+```
+
+**Advantages:**
+- ✅ No accounts or external infrastructure
+- ✅ Works in air-gapped/offline environments
+- ✅ Simple one-time setup
+- ✅ Version management through file shares
+
+**For centralized distribution**, see Options 1-3 below.
+
+---
+
+## Chocolatey (Windows)
+
+### Prerequisites
+
+- Chocolatey installed: https://chocolatey.org/install
+- (Only for public community repo) Chocolatey maintainer account at chocolatey.org
+
+### Building the Chocolatey Package
+
+```bash
+# 1. Build MSI installer first
+python build/scripts/build_windows.py --msi
+
+# 2. Calculate SHA256 checksum of the MSI
+certutil -hashfile "build/dist/windows/WebDropBridge_Setup.msi" SHA256
+
+# 3. Update the checksum in build/chocolatey/tools/chocolateyInstall.ps1
+#    Replace: $Checksum = ''
+#    With:    $Checksum = 'YOUR_SHA256_HASH'
+
+# 4. Update version in chocolatey/webdrop-bridge.nuspec
+#    <version>0.8.0</version>
+
+# 5. Create the package
+cd build/chocolatey
+choco pack webdrop-bridge.nuspec
+```
+
+This creates `webdrop-bridge.0.8.0.nupkg`
+
+### Publishing to Chocolatey
+
+**Option 1: Internal NuGet Repository (Recommended for HIM)**
+
+Host on your own NuGet server (Azure Artifacts, Artifactory, ProGet, etc.):
+
+```powershell
+# Configure Chocolatey to use internal repository
+choco source add -n=internal-repo -s "https://your-artifactory.internal/nuget/chocolatey/"
+
+# Push package to internal repo
+nuget push webdrop-bridge.0.8.0.nupkg -Source https://your-artifactory.internal/nuget/chocolatey/ -ApiKey YOUR_API_KEY
+
+# Users install from internal repo (already configured)
+choco install webdrop-bridge
+```
+
+**Option 2: Community Repository (chocolatey.org)**
+
+If you want public distribution (requires community maintainer account):
+
+```bash
+# Push to community repo
+choco push webdrop-bridge.0.8.0.nupkg --api-key YOUR_CHOCOLATEY_API_KEY
+```
+
+**Option 3: No Repository (Direct Distribution)**
+
+Share the `.nupkg` file directly, users install locally:
+
+```powershell
+# User downloads webdrop-bridge.0.8.0.nupkg and runs:
+choco install webdrop-bridge.0.8.0.nupkg -s C:\path\to\package\folder
+```
+
+### User Installation
+
+Depending on your chosen distribution:
+
+```powershell
+# If using internal repository
+choco install webdrop-bridge
+
+# If using community repo (chocolatey.org)
+choco install webdrop-bridge
+
+# If distributing directly
+choco install webdrop-bridge.0.8.0.nupkg -s "\\network\share\packages"
+```
+
+## Homebrew (macOS)
+
+### Prerequisites
+
+- Homebrew installed: https://brew.sh
+- GitHub or Gitea account for hosting tap repository
+
+### Two Approaches
+
+#### Option A: Local Tap (Recommended for HIM)
+
+Create a custom tap repository to distribute your formula without submitting to official Homebrew.
+
+**Setup:**
+
+```bash
+# Create tap repository
+mkdir homebrew-webdrop-bridge
+cd homebrew-webdrop-bridge
+
+# Create structure
+mkdir -p Formula
+cp ../build/homebrew/webdrop-bridge.rb Formula/
+
+# Initialize git repo and push to Forgejo
+git init
+git add .
+git commit -m "Add webdrop-bridge formula"
+git remote add origin https://git.him-tools.de/HIM-public/homebrew-webdrop-bridge.git
+git push -u origin main
+```
+
+**User Installation:**
+
+```bash
+# Add tap
+brew tap HIM-public/webdrop-bridge https://git.him-tools.de/HIM-public/homebrew-webdrop-bridge.git
+
+# Install
+brew install webdrop-bridge
+
+# Upgrade
+brew upgrade webdrop-bridge
+```
+
+#### Option B: Official Homebrew Repository
+
+Submit to `homebrew/casks` (requires more maintenance but no separate tap):
+
+1. Fork https://github.com/Homebrew/homebrew-casks
+2. Create pull request with Cask file
+3. Homebrew maintainers review and merge
+4. Users install via `brew install --cask webdrop-bridge`
+
+### Building the Homebrew Package (Locally)
+
+```bash
+# 1. Build DMG installer
+bash build/scripts/build_macos.sh
+
+# 2. Calculate SHA256 checksum
+shasum -a 256 "build/dist/macos/WebDropBridge_Setup.dmg"
+
+# 3. Update formula with checksum and URL
+#    build/homebrew/webdrop-bridge.rb
+#    - url: https://git.him-tools.de/...releases/download/vX.X.X/WebDropBridge_Setup.dmg
+#    - sha256: YOUR_SHA256_HASH
+```
+
+### Testing Homebrew Formula Locally
+
+```bash
+# Validate formula syntax
+brew audit --formula build/homebrew/webdrop-bridge.rb
+
+# Install from local formula
+brew install build/homebrew/webdrop-bridge.rb
+
+# Verify installation
+brew list webdrop-bridge
+webdrop-bridge --version  # If CLI exists, or check Applications folder
+```
+
+## Publishing Workflow
+
+### Step 1: Build Release
+
+```bash
+# Release v0.8.0
+
+# Windows MSI
+python build/scripts/build_windows.py --msi
+
+# macOS DMG
+bash build/scripts/build_macos.sh
+```
+
+### Step 2: Create Forgejo Release
+
+Tag and upload installers to Forgejo:
+
+```bash
+git tag -a v0.8.0 -m "Release 0.8.0"
+git push upstream v0.8.0
+
+# Upload MSI and DMG to Forgejo release page
+```
+
+### Step 3: Calculate Checksums
+
+```bash
+# Windows
+certutil -hashfile WebDropBridge_Setup.msi SHA256
+
+# macOS
+shasum -a 256 WebDropBridge_Setup.dmg
+```
+
+### Step 4: Update Package Manager Files
+
+**Chocolatey** (`build/chocolatey/tools/chocolateyInstall.ps1`):
+```powershell
+$Checksum = 'WINDOWS_SHA256_HASH'
+```
+
+**Homebrew** (`build/homebrew/webdrop-bridge.rb`):
+```ruby
+sha256 "MACOS_SHA256_HASH"
+```
+
+### Step 5: Test Package Installation
+
+**Chocolatey:**
+```powershell
+cd build/chocolatey
+choco pack
+choco install webdrop-bridge.0.8.0.nupkg -s .
+```
+
+**Homebrew (with tap):**
+```bash
+brew install ./build/homebrew/webdrop-bridge.rb
+```
+
+### Step 6: Publish
+
+**Chocolatey:**
+```powershell
+choco push webdrop-bridge.0.8.0.nupkg --api-key YOUR_KEY
+```
+
+**Homebrew:**
+- If using local tap: Push to Forgejo repository
+- If using official: Submit pull request to homebrew-casks
+
+## Update Workflow
+
+### For Subsequent Releases (e.g., v0.9.0)
+
+1. Build new installers (MSI/DMG)
+2. Create Forgejo release with new version
+3. Calculate new checksums
+4. Update version and checksums in:
+   - `build/chocolatey/webdrop-bridge.nuspec`
+   - `build/chocolatey/tools/chocolateyInstall.ps1`
+   - `build/homebrew/webdrop-bridge.rb`
+5. Test locally
+6. Publish to package managers
+
+## Configuration in Package Managers
+
+### Chocolatey
+
+Located in: `build/chocolatey/tools/chocolateyInstall.ps1`
+
+Key variables to update per release:
+- `$Version` - Application version
+- `$Url` - Download URL (Forgejo release)
+- `$Checksum` - SHA256 hash of MSI
+- `$ChecksumType` - Type of hash (sha256)
+
+### Homebrew
+
+Located in: `build/homebrew/webdrop-bridge.rb`
+
+Key variables to update per release:
+- `version` - Application version
+- `url` - Download URL (Forgejo release)
+- `sha256` - SHA256 hash of DMG
+
+## Automatic Updates
+
+### Via Package Managers
+
+When users install via Chocolatey/Homebrew, they receive updates through:
+
+```bash
+# Chocolatey
+choco upgrade webdrop-bridge
+
+# Homebrew
+brew upgrade webdrop-bridge
+```
+
+### Built-in Auto-Update (Fallback)
+
+WebDropBridge also includes built-in auto-update mechanism that:
+1. Checks Forgejo releases API on startup
+2. Notifies user of available updates
+3. Downloads and installs directly (bypasses package manager)
+
+This works for:
+- Direct downloads via wget
+- Standalone installer use
+- Users who skip package manager route
+
+## Troubleshooting
+
+### Chocolatey Issues
+
+**Package won't install:**
+- Verify checksum: `certutil -hashfile WebDropBridge_Setup.msi SHA256`
+- Check MSI exists at URL: `wget URL`
+- Verify SHA256 matches in `chocolateyInstall.ps1`
+
+**Uninstall fails:**
+- Try manual uninstall first
+- Then recreate the Chocolatey package
+
+### Homebrew Issues
+
+**Formula won't install:**
+- Validate syntax: `brew audit --formula webdrop-bridge.rb`
+- Check URL is accessible: `curl -I URL`
+- Verify SHA256: `shasum -a 256 WebDropBridge_Setup.dmg`
+
+**Upgrade fails:**
+- Remove old version: `brew uninstall webdrop-bridge`
+- Reinstall: `brew install webdrop-bridge`
+
+## References
+
+- **Chocolatey Documentation**: https://docs.chocolatey.org/
+- **Homebrew Formula Reference**: https://docs.brew.sh/Formula-Cookbook
+- **Homebrew Cask**: https://docs.brew.sh/Cask-Cookbook
+- **Forgejo Releases**: https://git.him-tools.de/HIM-public/webdrop-bridge/releases
+
+---
+
+**Distribution Strategy Options for HIM:**
+
+1. **Easiest: Direct Distribution** ✅
+   - Share `.nupkg` file via file share or email
+   - Users: `choco install webdrop-bridge.0.8.0.nupkg -s "\\share\packages"`
+   - No infrastructure needed
+   - No maintainer account required
+
+2. **Better: Internal NuGet Repository** ✅ (Recommended)
+   - Host on Azure Artifacts or Artifactory
+   - Professional package management
+   - Automatic updates with `choco upgrade`
+   - Users: `choco install webdrop-bridge` (pre-configured)
+
+3. **Public: Chocolatey Community** (Optional)
+   - Publish to chocolatey.org (requires maintainer account + vetting)
+   - Widest distribution
+   - Public users: `choco install webdrop-bridge`