diff --git a/.github/workflows/test-chocolatey.yml b/.github/workflows/test-chocolatey.yml
new file mode 100644
index 0000000..2d87c6d
--- /dev/null
+++ b/.github/workflows/test-chocolatey.yml
@@ -0,0 +1,83 @@
+name: Test Chocolatey Package
+
+on:
+  pull_request:
+    paths:
+      - 'packaging/chocolatey/**'
+      - '.github/workflows/test-chocolatey.yml'
+  push:
+    branches: [main]
+    paths:
+      - 'packaging/chocolatey/**'
+      - '.github/workflows/test-chocolatey.yml'
+
+jobs:
+  test-chocolatey:
+    runs-on: windows-latest
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Set up Go
+        uses: actions/setup-go@v5
+        with:
+          go-version: '1.22'
+
+      - name: Build binary for testing
+        run: go build -o packaging/chocolatey/tools/cfl.exe ./cmd/cfl
+
+      - name: Prepare test package
+        shell: pwsh
+        working-directory: packaging/chocolatey
+        run: |
+          # Replace placeholder version with test version (must not be prerelease)
+          (Get-Content confluence-cli.nuspec) `
+            -replace '<version>0.0.0</version>', '<version>0.0.1</version>' |
+            Set-Content confluence-cli.nuspec
+
+          # Create a simple install script that uses the local binary
+          # (the real script downloads from GitHub, but we test structure here)
+          @'
+          $ErrorActionPreference = 'Stop'
+          $toolsDir = Split-Path -Parent $MyInvocation.MyCommand.Definition
+
+          # Binary is already in tools/ from CI build
+          Write-Host "confluence-cli installed from local build for testing"
+
+          # Exclude non-executables from shimming
+          New-Item "$toolsDir\LICENSE.ignore" -Type File -Force | Out-Null
+          New-Item "$toolsDir\README.md.ignore" -Type File -Force | Out-Null
+          '@ | Set-Content tools/chocolateyInstall.ps1
+
+      - name: Pack Chocolatey package
+        shell: pwsh
+        working-directory: packaging/chocolatey
+        run: choco pack
+
+      - name: Install package locally
+        shell: pwsh
+        working-directory: packaging/chocolatey
+        run: choco install confluence-cli -dv -s . --force
+
+      - name: Verify installation
+        shell: pwsh
+        run: |
+          Write-Host "Testing cfl --version..."
+          cfl --version
+          if ($LASTEXITCODE -ne 0) {
+            Write-Error "cfl --version failed"
+            exit 1
+          }
+          Write-Host "cfl is working!"
+
+      - name: Test uninstall
+        shell: pwsh
+        run: |
+          choco uninstall confluence-cli -y
+
+          # Verify cfl is no longer available
+          $cflPath = Get-Command cfl -ErrorAction SilentlyContinue
+          if ($cflPath) {
+            Write-Error "cfl should not be available after uninstall"
+            exit 1
+          }
+          Write-Host "Uninstall successful!"
diff --git a/CLAUDE.md b/CLAUDE.md
index 214a7dc..ae39a8d 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -191,3 +191,21 @@ Releases are automated via release-please. When PRs merge to main with conventio
 **Before merging a PR:** Run `/release-notes` to generate release notes and update the PR description.
 
 **After merging:** release-please creates a Release PR. Merging that PR triggers the full release (GitHub Release + Homebrew tap update).
+
+## Packaging
+
+Distribution packages are in `packaging/`:
+
+```
+packaging/
+├── chocolatey/              # Windows Chocolatey package
+│   ├── confluence-cli.nuspec
+│   ├── tools/chocolateyInstall.ps1
+│   ├── tools/chocolateyUninstall.ps1
+│   └── README.md            # Publishing instructions
+└── homebrew/
+    └── README.md            # Points to GoReleaser config
+```
+
+- **Homebrew**: Managed by GoReleaser, published to [open-cli-collective/homebrew-tap](https://github.com/open-cli-collective/homebrew-tap)
+- **Chocolatey**: Manual publish process documented in `packaging/chocolatey/README.md`
diff --git a/packaging/chocolatey/README.md b/packaging/chocolatey/README.md
new file mode 100644
index 0000000..0a525cc
--- /dev/null
+++ b/packaging/chocolatey/README.md
@@ -0,0 +1,96 @@
+# Chocolatey Package for confluence-cli
+
+This directory contains the Chocolatey package definition for distributing confluence-cli on Windows.
+
+## Package Structure
+
+```
+packaging/chocolatey/
+├── confluence-cli.nuspec    # Package manifest
+├── tools/
+│   ├── chocolateyInstall.ps1    # Downloads and installs from GitHub Releases
+│   └── chocolateyUninstall.ps1  # Cleanup script
+└── README.md
+```
+
+## Local Testing
+
+### Prerequisites
+
+- Windows with [Chocolatey installed](https://chocolatey.org/install)
+- PowerShell (Admin)
+
+### Build the Package
+
+```powershell
+cd packaging/chocolatey
+
+# Update version in nuspec to match a real release (e.g., 0.10.0)
+# Then pack:
+choco pack
+```
+
+This creates `confluence-cli.<version>.nupkg`.
+
+### Install Locally
+
+```powershell
+# Install from local package
+choco install confluence-cli -s . --force
+
+# Verify
+cfl --version
+
+# Uninstall
+choco uninstall confluence-cli
+```
+
+## Publishing to Chocolatey Community Repository
+
+### First-Time Setup
+
+1. Create an account at https://community.chocolatey.org
+2. Get your API key from https://community.chocolatey.org/account
+3. Configure your API key:
+   ```powershell
+   choco apikey --key <your-api-key> --source https://push.chocolatey.org/
+   ```
+
+### Publishing a New Version
+
+1. Update the `<version>` in `confluence-cli.nuspec` to match the GitHub release
+2. Pack the package:
+   ```powershell
+   choco pack
+   ```
+3. Push to Chocolatey:
+   ```powershell
+   choco push confluence-cli.<version>.nupkg --source https://push.chocolatey.org/
+   ```
+
+### Moderation Process
+
+- New packages go through moderation (typically 1-3 days)
+- Automated checks verify the package downloads correctly
+- Human moderators review the package
+- Status updates are sent via email
+
+## Architecture Support
+
+The install script automatically detects Windows architecture:
+
+| Architecture | Download |
+|--------------|----------|
+| ARM64 | `cfl_<version>_windows_arm64.zip` |
+| x64 | `cfl_<version>_windows_amd64.zip` |
+| x86 | Not supported (error) |
+
+## Updating for New Releases
+
+When a new version is released on GitHub:
+
+1. Update `<version>` in `confluence-cli.nuspec`
+2. Test locally with `choco pack && choco install confluence-cli -s . --force`
+3. Push to Chocolatey with `choco push`
+
+The install script dynamically fetches checksums from `checksums.txt` in the GitHub release, so no checksum updates are needed in the package files.
diff --git a/packaging/chocolatey/confluence-cli.nuspec b/packaging/chocolatey/confluence-cli.nuspec
new file mode 100644
index 0000000..97f132b
--- /dev/null
+++ b/packaging/chocolatey/confluence-cli.nuspec
@@ -0,0 +1,32 @@
+<?xml version="1.0" encoding="utf-8"?>
+<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
+  <metadata>
+    <id>confluence-cli</id>
+    <version>0.0.0</version>
+    <title>Confluence CLI</title>
+    <authors>Open CLI Collective</authors>
+    <owners>rianjs</owners>
+    <licenseUrl>https://github.com/open-cli-collective/confluence-cli/blob/main/LICENSE</licenseUrl>
+    <projectUrl>https://github.com/open-cli-collective/confluence-cli</projectUrl>
+    <projectSourceUrl>https://github.com/open-cli-collective/confluence-cli</projectSourceUrl>
+    <packageSourceUrl>https://github.com/open-cli-collective/confluence-cli/tree/main/packaging/chocolatey</packageSourceUrl>
+    <bugTrackerUrl>https://github.com/open-cli-collective/confluence-cli/issues</bugTrackerUrl>
+    <requireLicenseAcceptance>false</requireLicenseAcceptance>
+    <description>A command-line interface for Atlassian Confluence Cloud. Provides markdown-first page management with automatic conversion between Markdown and Confluence's storage format.
+
+Features:
+- Create, edit, view, and delete Confluence pages
+- Bidirectional Markdown to Confluence HTML conversion
+- Attachment management (upload, download, list)
+- Space listing and search
+- Support for Confluence macros (TOC, panels, expand)
+
+Binary: cfl.exe</description>
+    <summary>Command-line interface for Atlassian Confluence Cloud</summary>
+    <releaseNotes>https://github.com/open-cli-collective/confluence-cli/releases</releaseNotes>
+    <tags>confluence atlassian cli markdown wiki documentation</tags>
+  </metadata>
+  <files>
+    <file src="tools\**" target="tools" />
+  </files>
+</package>
diff --git a/packaging/chocolatey/tools/chocolateyInstall.ps1 b/packaging/chocolatey/tools/chocolateyInstall.ps1
new file mode 100644
index 0000000..5b088c8
--- /dev/null
+++ b/packaging/chocolatey/tools/chocolateyInstall.ps1
@@ -0,0 +1,43 @@
+$ErrorActionPreference = 'Stop'
+
+$version = $env:ChocolateyPackageVersion
+$toolsDir = Split-Path -Parent $MyInvocation.MyCommand.Definition
+
+# Architecture detection with ARM64 support
+if ($env:PROCESSOR_ARCHITECTURE -eq 'ARM64') {
+    $arch = 'arm64'
+} elseif ([Environment]::Is64BitOperatingSystem) {
+    $arch = 'amd64'
+} else {
+    throw "32-bit Windows is not supported. confluence-cli requires 64-bit Windows."
+}
+
+$baseUrl = "https://github.com/open-cli-collective/confluence-cli/releases/download/v${version}"
+$zipFile = "cfl_${version}_windows_${arch}.zip"
+$url = "${baseUrl}/${zipFile}"
+$checksumsUrl = "${baseUrl}/checksums.txt"
+
+# Fetch checksums and extract the one for our architecture
+$checksums = (Invoke-WebRequest -Uri $checksumsUrl -UseBasicParsing).Content
+$checksumLine = $checksums -split "`n" | Where-Object { $_ -match $zipFile }
+if (-not $checksumLine) {
+    throw "Could not find checksum for ${zipFile} in checksums.txt"
+}
+$checksum = ($checksumLine -split '\s+')[0]
+
+Write-Host "Installing confluence-cli ${version} for Windows ${arch}..."
+Write-Host "URL: ${url}"
+Write-Host "Checksum (SHA256): ${checksum}"
+
+Install-ChocolateyZipPackage -PackageName $env:ChocolateyPackageName `
+    -Url $url `
+    -UnzipLocation $toolsDir `
+    -Checksum $checksum `
+    -ChecksumType 'sha256'
+
+# Exclude non-executables from shimming
+# Chocolatey auto-creates shims for .exe files; .ignore files prevent shimming other files
+New-Item "$toolsDir\LICENSE.ignore" -Type File -Force | Out-Null
+New-Item "$toolsDir\README.md.ignore" -Type File -Force | Out-Null
+
+Write-Host "confluence-cli installed successfully. Run 'cfl --help' to get started."
diff --git a/packaging/chocolatey/tools/chocolateyUninstall.ps1 b/packaging/chocolatey/tools/chocolateyUninstall.ps1
new file mode 100644
index 0000000..8c1db3d
--- /dev/null
+++ b/packaging/chocolatey/tools/chocolateyUninstall.ps1
@@ -0,0 +1,15 @@
+$ErrorActionPreference = 'Stop'
+
+$toolsDir = Split-Path -Parent $MyInvocation.MyCommand.Definition
+
+Write-Host "Uninstalling confluence-cli..."
+
+# Remove extracted files
+Remove-Item "$toolsDir\cfl.exe" -Force -ErrorAction SilentlyContinue
+Remove-Item "$toolsDir\LICENSE" -Force -ErrorAction SilentlyContinue
+Remove-Item "$toolsDir\README.md" -Force -ErrorAction SilentlyContinue
+
+# Remove .ignore files created during install
+Remove-Item "$toolsDir\*.ignore" -Force -ErrorAction SilentlyContinue
+
+Write-Host "confluence-cli has been uninstalled."
diff --git a/packaging/homebrew/README.md b/packaging/homebrew/README.md
new file mode 100644
index 0000000..f003107
--- /dev/null
+++ b/packaging/homebrew/README.md
@@ -0,0 +1,17 @@
+# Homebrew Distribution
+
+Homebrew packaging is managed automatically by [GoReleaser](https://goreleaser.com/) during the release process.
+
+## Configuration
+
+The Homebrew cask configuration lives in [`.goreleaser.yml`](../../.goreleaser.yml) under the `homebrew_casks` section.
+
+## Tap Repository
+
+The generated cask is published to: https://github.com/open-cli-collective/homebrew-tap
+
+## Installation
+
+```bash
+brew install open-cli-collective/tap/cfl
+```