diff --git a/DEVELOPMENT_PLAN.md b/DEVELOPMENT_PLAN.md
index fa8146e..e5460e6 100644
--- a/DEVELOPMENT_PLAN.md
+++ b/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
diff --git a/QUICKSTART.md b/QUICKSTART.md
index f32ce7c..5c9611e 100644
--- a/QUICKSTART.md
+++ b/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)
diff --git a/README.md b/README.md
index ad53590..191e608 100644
--- a/README.md
+++ b/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
diff --git a/build/chocolatey/tools/chocolateyInstall.ps1 b/build/chocolatey/tools/chocolateyInstall.ps1
new file mode 100644
index 0000000..619370a
--- /dev/null
+++ b/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 $TempDir -Recurse -Force -ErrorAction SilentlyContinue
+ }
+}
diff --git a/build/chocolatey/tools/chocolateyUninstall.ps1 b/build/chocolatey/tools/chocolateyUninstall.ps1
new file mode 100644
index 0000000..599426b
--- /dev/null
+++ b/build/chocolatey/tools/chocolateyUninstall.ps1
@@ -0,0 +1,38 @@
+$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: $_"
+}
diff --git a/build/chocolatey/webdrop-bridge.nuspec b/build/chocolatey/webdrop-bridge.nuspec
new file mode 100644
index 0000000..18b160c
--- /dev/null
+++ b/build/chocolatey/webdrop-bridge.nuspec
@@ -0,0 +1,28 @@
+
+
+
+ webdrop-bridge
+ 0.8.0
+ https://git.him-tools.de/HIM-public/webdrop-bridge
+ HIM-public
+ WebDrop Bridge
+ HIM-public
+ https://git.him-tools.de/HIM-public/webdrop-bridge/blob/main/LICENSE
+ https://git.him-tools.de/HIM-public/webdrop-bridge
+ https://git.him-tools.de/HIM-public/webdrop-bridge/issues
+
+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.
+
+ Intelligent drag-and-drop file bridge for web to desktop applications
+ https://git.him-tools.de/HIM-public/webdrop-bridge/releases/tag/v0.8.0
+ drag-drop file-transfer qt pyside6 desktop automation
+
+
+
+
+
+
+
+
diff --git a/build/homebrew/webdrop-bridge.rb b/build/homebrew/webdrop-bridge.rb
new file mode 100644
index 0000000..605f03b
--- /dev/null
+++ b/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
diff --git a/build/package-managers/README.md b/build/package-managers/README.md
new file mode 100644
index 0000000..7f0a400
--- /dev/null
+++ b/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 ``
+ - `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/)
diff --git a/docs/PACKAGE_MANAGER_SUPPORT.md b/docs/PACKAGE_MANAGER_SUPPORT.md
new file mode 100644
index 0000000..e49d914
--- /dev/null
+++ b/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
+# 0.8.0
+
+# 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`