diff --git a/WARP.md b/WARP.md
index 8735388..e4a5042 100644
--- a/WARP.md
+++ b/WARP.md
@@ -16,10 +16,19 @@ This file provides guidance to WARP (warp.dev) when working with code in this re
 - Run CLI without installing: `cargo run --bin cull-gmail -- --help`
 - Test a single test by pattern: `cargo test test_rules_new_creates_default_rules`
 
+### Init Command Examples
+- Interactive setup: `cargo run --bin cull-gmail -- init --interactive`
+- Dry-run preview: `cargo run --bin cull-gmail -- init --dry-run`
+- Force overwrite: `cargo run --bin cull-gmail -- init --force`
+- Custom config dir: `cargo run --bin cull-gmail -- init --config-dir /tmp/test-config`
+
 ### Special Tests
 - Run ignored Gmail API integration test: `cargo test --test gmail_message_list_integration -- --ignored`
   - Requires valid OAuth2 credentials configured
   - Only use with test Gmail account
+- Run ignored init OAuth integration test: `CULL_GMAIL_TEST_CREDENTIAL_FILE=/path/to/creds.json cargo test --test init_integration_tests test_init_oauth_integration -- --ignored`
+  - Requires `CULL_GMAIL_TEST_CREDENTIAL_FILE` environment variable with path to valid OAuth2 credential file
+  - Tests complete init flow including OAuth2 token generation
 
 ## High-level Architecture
 
@@ -35,6 +44,7 @@ This file provides guidance to WARP (warp.dev) when working with code in this re
 - **CLI**: Command-line interface with subcommands for `labels`, `messages`, `rules`, and `token`; implements dry-run-first behavior for safety
 
 ### CLI Subcommands
+- `init` - Initialize cull-gmail configuration, credentials, and OAuth2 tokens with guided setup
 - `labels` - List and inspect available Gmail labels
 - `messages` - Query, filter, and perform batch operations on Gmail messages
 - `rules` - Configure and execute automated message retention rules
diff --git a/docs/cli_init.md b/docs/cli_init.md
new file mode 100644
index 0000000..e2dfe69
--- /dev/null
+++ b/docs/cli_init.md
@@ -0,0 +1,324 @@
+# cull-gmail init Command
+
+The `init` command provides guided setup for the cull-gmail application, creating the configuration directory, installing OAuth2 credentials, generating default configuration files, and completing the initial Gmail API authentication.
+
+## Overview
+
+The initialization process performs these steps:
+
+1. **Configuration Directory**: Create or verify the configuration directory
+2. **Credential Installation**: Copy and validate OAuth2 credential file (if provided)  
+3. **Configuration Generation**: Create `cull-gmail.toml` with safe defaults
+4. **Rules Template**: Generate `rules.toml` with example retention rules
+5. **Token Directory**: Ensure OAuth2 token cache directory exists
+6. **Authentication**: Complete OAuth2 flow to generate and persist tokens
+
+## Command Syntax
+
+```bash
+cull-gmail init [OPTIONS]
+```
+
+## Options
+
+### Required Configuration
+
+- `--config-dir <DIR>`: Configuration directory path (default: `h:.cull-gmail`)
+  - Supports path prefixes:
+    - `h:path` - Relative to home directory
+    - `c:path` - Relative to current directory  
+    - `r:path` - Relative to filesystem root
+    - `path` - Use path as-is
+
+### OAuth2 Credentials
+
+- `--credential-file <PATH>`: Path to OAuth2 credential JSON file
+  - Should be downloaded from Google Cloud Console
+  - Must be for Desktop application type
+  - Will be copied to config directory as `credential.json`
+
+### Execution Modes
+
+- `--dry-run`: Preview all planned actions without making changes
+  - Shows what files would be created
+  - Displays OAuth2 authentication plan
+  - Safe to run multiple times
+
+- `--interactive` / `-i`: Enable interactive prompts and confirmations
+  - Prompts for missing credential file path
+  - Asks for confirmation before overwriting files
+  - Recommended for first-time users
+
+- `--force`: Overwrite existing files without prompting
+  - Creates timestamped backups (e.g., `config.bak-20231201120000`)
+  - Use with caution as it replaces existing configuration
+
+## Usage Examples
+
+### Basic Setup
+
+```bash
+# Basic initialization with default settings
+cull-gmail init
+
+# Custom configuration directory
+cull-gmail init --config-dir /custom/path
+```
+
+### Interactive Setup
+
+```bash
+# Interactive setup (recommended for first use)
+cull-gmail init --interactive
+
+# Interactive with credential file
+cull-gmail init --interactive --credential-file ~/Downloads/client_secret.json
+```
+
+### Planning and Preview
+
+```bash
+# Preview what would be created
+cull-gmail init --dry-run
+
+# Preview with specific options
+cull-gmail init --config-dir ~/.cull-gmail --credential-file credentials.json --dry-run
+```
+
+### Force Overwrite
+
+```bash
+# Recreate configuration with backups
+cull-gmail init --force
+
+# Force with specific credential file
+cull-gmail init --force --credential-file new_credentials.json
+```
+
+## File Structure Created
+
+The init command creates the following structure:
+
+```
+~/.cull-gmail/                  # Configuration directory
+├── cull-gmail.toml             # Main configuration
+├── rules.toml                  # Retention rules template  
+├── credential.json             # OAuth2 credentials (if provided)
+└── gmail1/                     # OAuth2 token cache
+    └── [token files]           # Generated after OAuth2 flow
+```
+
+### Configuration File (`cull-gmail.toml`)
+
+```toml
+# cull-gmail configuration
+# This file configures the cull-gmail application.
+
+# OAuth2 credential file (relative to config_root)
+credential_file = "credential.json"
+
+# Configuration root directory  
+config_root = "h:.cull-gmail"
+
+# Rules configuration file
+rules = "rules.toml"
+
+# Default execution mode (false = dry-run, true = execute)
+# Set to false for safety - you can override with --execute flag
+execute = false
+
+# Environment variable name for token cache (for ephemeral environments)
+token_cache_env = "CULL_GMAIL_TOKEN_CACHE"
+```
+
+### Rules File (`rules.toml`)
+
+```toml
+# Example rules for cull-gmail
+# Each rule targets a Gmail label and specifies an action.
+# 
+# Actions:
+#   - "Trash" is recoverable (messages go to Trash folder ~30 days)
+#   - "Delete" is irreversible (messages are permanently deleted)
+#
+# Time formats:
+#   - "older_than:30d" (30 days)
+#   - "older_than:6m" (6 months) 
+#   - "older_than:2y" (2 years)
+#
+# Example rule for promotional emails:
+# [[rules]]
+# id = 1
+# label = "Promotions"
+# query = "category:promotions older_than:30d"
+# action = "Trash"
+#
+# Example rule for old newsletters:
+# [[rules]]
+# id = 2
+# label = "Updates"
+# query = "category:updates older_than:90d"
+# action = "Trash"
+#
+# Uncomment and modify the examples above to create your own rules.
+# Run 'cull-gmail rules run --dry-run' to test rules before execution.
+```
+
+## OAuth2 Setup Guide
+
+### 1. Google Cloud Console Setup
+
+1. Visit [Google Cloud Console](https://console.cloud.google.com/)
+2. Create a new project or select an existing one
+3. Enable the Gmail API:
+   - Go to "APIs & Services" > "Library"
+   - Search for "Gmail API" and enable it
+4. Create OAuth2 credentials:
+   - Go to "APIs & Services" > "Credentials"
+   - Click "Create Credentials" > "OAuth client ID"
+   - Choose "Desktop application"
+   - Download the JSON file
+
+### 2. OAuth2 Authentication Flow
+
+When you run `cull-gmail init` with a credential file:
+
+1. The credential file is validated and copied securely
+2. A web browser opens for Google authentication
+3. You grant Gmail access permissions
+4. Tokens are automatically saved to the `gmail1/` directory
+5. Future runs use the cached tokens (no browser needed)
+
+### 3. Troubleshooting OAuth2
+
+**Error: Invalid credential file format**
+- Ensure you downloaded the JSON file for "Desktop application"
+- Mobile or web application credentials won't work
+
+**Error: Gmail API not enabled**
+- Return to Google Cloud Console
+- Enable the Gmail API for your project
+
+**Error: OAuth2 authentication failed**
+- Check your internet connection
+- Verify the credential file is not corrupted
+- Try re-downloading credentials from Google Cloud Console
+
+**Error: Redirect URI mismatch**
+- Desktop application credentials should work automatically
+- If issues persist, check the redirect URIs in Google Cloud Console
+
+## Security Considerations
+
+### File Permissions
+
+The init command sets secure permissions on created files:
+
+- **Configuration files**: `0644` (owner read/write, others read)
+- **Credential files**: `0600` (owner read/write only)  
+- **Token directory**: `0700` (owner access only)
+
+### Backup Safety
+
+When using `--force` or accepting overwrites in `--interactive` mode:
+
+- Existing files are backed up with timestamps
+- Backup format: `filename.bak-YYYYmmddHHMMSS`
+- Original files are preserved until manually removed
+
+### Credential Handling
+
+- Credential files are validated before copying
+- Files are copied with restricted permissions
+- OAuth2 tokens are stored securely in the token cache directory
+
+## Next Steps After Initialization
+
+After successful initialization:
+
+```bash
+# 1. Test Gmail connection
+cull-gmail labels
+
+# 2. Review the rules template
+cull-gmail rules run --dry-run
+
+# 3. Customize rules.toml as needed
+# Edit ~/.cull-gmail/rules.toml
+
+# 4. Test your rules safely
+cull-gmail rules run --dry-run
+
+# 5. Execute rules for real (when ready)
+cull-gmail rules run --execute
+```
+
+## Error Handling
+
+### Common Error Scenarios
+
+**Configuration Already Exists**
+```bash
+# Error message shown
+File I/O error: Configuration file already exists: ~/.cull-gmail/cull-gmail.toml
+Use --force to overwrite or --interactive for prompts
+
+# Solutions
+cull-gmail init --force                    # Overwrite with backup
+cull-gmail init --interactive             # Prompt for each conflict
+```
+
+**Missing Credential File**
+```bash
+# Error message shown  
+File I/O error: Credential file not found: /path/to/file.json
+
+# Solution
+# Ensure the file path is correct and the file exists
+cull-gmail init --credential-file /correct/path/to/file.json
+```
+
+**Permission Errors**
+```bash
+# Error message shown
+File I/O error: Failed to create directory: Permission denied
+
+# Solutions
+# Ensure you have write permission to the target directory
+# Or choose a different config directory
+cull-gmail init --config-dir ~/my-cull-gmail
+```
+
+## Integration with Other Commands
+
+The `init` command integrates seamlessly with other cull-gmail features:
+
+### Token Export/Import
+
+```bash
+# After initialization, export tokens for ephemeral environments
+cull-gmail token export > my-tokens.env
+
+# In another environment, set the token cache
+export CULL_GMAIL_TOKEN_CACHE="$(cat my-tokens.env)"
+cull-gmail labels  # Uses imported tokens
+```
+
+### Rules Management
+
+```bash
+# After initialization, manage rules
+cull-gmail rules config rules add
+cull-gmail rules config label add 1 "old-emails"
+cull-gmail rules config action 1 trash
+```
+
+### Message Operations
+
+```bash
+# After initialization, work with messages
+cull-gmail messages -l "Promotions" list
+cull-gmail messages -Q "older_than:30d" trash --dry-run
+```
+
+This comprehensive setup makes cull-gmail ready for automated Gmail message management with full OAuth2 authentication and secure configuration handling.
\ No newline at end of file
diff --git a/docs/readme/head.md b/docs/readme/head.md
index b943ba6..9dfd7d9 100644
--- a/docs/readme/head.md
+++ b/docs/readme/head.md
@@ -29,13 +29,33 @@
 
 The `cull-gmail` provides a software library and command line program to enable the culling of emails using the Gmail API.
 
+## Quick Start
+
+Get started with cull-gmail in minutes using the built-in setup command:
+
+1. **Get OAuth2 credentials** from [Google Cloud Console](https://console.cloud.google.com/)
+2. **Initialize cull-gmail** with guided setup:
+   ```bash
+   # Interactive setup (recommended)
+   cull-gmail init --interactive --credential-file ~/Downloads/client_secret.json
+   
+   # Or preview first
+   cull-gmail init --dry-run
+   ```
+3. **Verify your setup**:
+   ```bash
+   cull-gmail labels
+   ```
+
 ## Main Features
 
-- list labels and messages to aid planning rules
-- configure the rules list 
-- run the rules list 
-- run the rules list be default 
-- configure api client by file or environment variables
+- **Easy initialization**: Guided setup with OAuth2 credential validation and secure file handling
+- **Flexible configuration**: Support for file-based config, environment variables, and ephemeral tokens
+- **Safety first**: Dry-run mode by default, interactive confirmations, and timestamped backups
+- **Label management**: List and inspect Gmail labels for rule planning
+- **Message operations**: Query, filter, and perform batch operations on Gmail messages  
+- **Rule-based automation**: Configure retention rules with time-based filtering and automated actions
+- **Token portability**: Export/import OAuth2 tokens for containerized and CI/CD environments
 
 ### Running the optional Gmail integration test