diff --git a/docs/help.md b/docs/help.md
new file mode 100644
index 0000000..ecc0cf3
--- /dev/null
+++ b/docs/help.md
@@ -0,0 +1,172 @@
+# pwcli Help Documentation
+
+**pwcli** is a CLI for Photowall platform that provides commands for deployment, AWS operations, workflow automation, and more.
+
+## Usage
+
+Run `pwcli` to start the interactive menu, or use command shortcuts directly:
+
+```bash
+pwcli [command] [subcommand] [action]
+```
+
+### Command Shortcuts
+
+Commands can be executed using their aliases. For example:
+- `pwcli d ts s` → deployment testservers status
+- `pwcli a ps l` → aws parameterstore list
+- `pwcli wf g cb` → workflow git clean_old_branches
+
+---
+
+## Available Commands
+
+### 🤖 **ai** (alias: `ai`)
+AI-related commands
+
+#### Subcommands:
+- **promptcontextlibrary** (alias: `pcl`) - Copy context files to clipboard for AI prompts
+
+**Example:** `pwcli ai pcl`
+
+---
+
+### ☁️ **aws** (alias: `a`)
+AWS operations and management
+
+#### Subcommands:
+
+##### **ecs** (alias: `e`) - Working with ECS on AWS
+- **sshtestserver** (alias: `sts`) - SSH into a test server in ECS
+
+**Example:** `pwcli a e sts`
+
+##### **logs** (alias: `l`) - Tail a log in CloudWatch (WIP)
+
+**Example:** `pwcli a l`
+
+##### **parameterstore** (alias: `ps`) - Working with parameter store on AWS
+- **bulk-create** (alias: `bc`) - Bulk create parameters from JSON file
+- **create** (alias: `c`) - Create a new item in parameter store
+- **list** (alias: `l`) - List all parameters in parameter store
+- **update** (alias: `u`) - Update an existing item in parameter store
+
+**Examples:**
+- `pwcli a ps l` - List parameters
+- `pwcli a ps c` - Create parameter
+- `pwcli a ps bc` - Bulk create from JSON file
+
+##### **pipeline** (alias: `pl`) - Pipeline operations
+- **status** (alias: `s`) - View pipeline status with live tracking
+
+**Example:** `pwcli a pl s`
+
+##### **s3** (alias: `s3`) - Working with S3 on AWS
+- **clear_prints** (alias: `cp`) - Clear prints-dev bucket on S3
+- **print_on_station** (alias: `pos`) - Print on a real station (copies from dev to production)
+- **sync_images** (alias: `si`) - Sync images between S3 buckets
+
+**Examples:**
+- `pwcli a s3 si` - Sync images
+- `pwcli a s3 cp` - Clear prints
+
+---
+
+### 🚀 **deployment** (alias: `d`)
+Deployment and test server management
+
+#### Subcommands:
+
+##### **testservers** (alias: `ts`) - Deploy to testservers
+- **create** (alias: `c`) - Create new testserver on AWS
+- **delete** (alias: `d`) - Choose a testserver to delete
+- **status** (alias: `s`) - Show status for available testservers
+- **update** (alias: `u`) - Update stack with different branch
+
+**Examples:**
+- `pwcli d ts s` - View testserver status
+- `pwcli d ts c` - Create new testserver
+- `pwcli d ts u` - Update existing testserver
+
+---
+
+### 📧 **mandrill** (alias: `m`)
+Mandrill/Mailchimp email template operations
+
+#### Subcommands:
+- **fix_template** (alias: `ft`) - Remove incorrect artifacts caused by Mailchimp export to Mandrill
+
+**Example:** `pwcli m ft`
+
+---
+
+### ⚙️ **setup** (alias: `s`)
+Setup pwcli configuration
+
+#### Subcommands:
+- **settings** (alias: `se`) - Setup settings for pwcli (GitHub token, repo paths, API keys, etc.)
+
+**Example:** `pwcli setup settings` or `pwcli s se`
+
+---
+
+### 🧪 **test** (alias: `t`)
+Test commands
+
+#### Subcommands:
+- **routes** (alias: `r`) - Test pre-configured routes for 200 status on configured localhost
+
+**Example:** `pwcli t r`
+
+---
+
+### 🔄 **update** (alias: `up`)
+Update pwcli to the latest version from main branch and rebuild
+
+**Example:** `pwcli update` or `pwcli up`
+
+---
+
+### 🔧 **workflow** (alias: `wf`)
+Workflow tools for development
+
+#### Subcommands:
+
+##### **git** (alias: `g`) - Tools for git to make repo life easier
+- **clean_local_branches** (alias: `clb`) - Clean local branches without origin connection
+- **clean_old_branches** (alias: `cb`) - Prune remote and clean local branches if gone
+
+**Examples:**
+- `pwcli wf g cb` - Clean old branches
+- `pwcli wf g clb` - Clean local branches
+
+##### **setupissue** (alias: `si`) - Setup everything for an issue
+Creates a new branch from origin/master based on a GitHub issue
+
+**Example:** `pwcli wf si`
+
+---
+
+## Configuration
+
+Run `pwcli setup settings` to configure:
+- GitHub access token
+- Local photowall repository path
+- Mandrill API key
+- Localhost URL and credentials for testing
+
+Settings are stored in `~/.pwcli_settings`
+
+---
+
+## Tips
+
+- Use the interactive menu by running `pwcli` without arguments
+- Chain command aliases for faster execution: `pwcli d ts s`
+- Most commands require AWS CLI to be installed and configured
+- Some commands require settings to be configured first (run `pwcli setup settings`)
+
+---
+
+For more information, visit the repository or run commands interactively with `pwcli`
+
diff --git a/src/cli.ts b/src/cli.ts
index c67e723..69e75e0 100644
--- a/src/cli.ts
+++ b/src/cli.ts
@@ -1,4 +1,6 @@
 const { build } = require('gluegun');
+const fs = require('fs');
+const path = require('path');
 
 /**
  * Create the cli and kick it off
@@ -19,7 +21,32 @@ async function run(argv) {
       hidden: false,
       dashed: true,
       run: (toolbox) => {
-        toolbox.print.info('This is the help');
+        // Try to read and display the help markdown file
+        try {
+          // When compiled, __dirname is build/commands
+          // Help file is in docs/ at repo root
+          const helpPath = path.join(__dirname, '../docs/help.md');
+
+          if (fs.existsSync(helpPath)) {
+            const helpContent = fs.readFileSync(helpPath, 'utf8');
+            toolbox.print.info(helpContent);
+          } else {
+            // Fallback if help file not found
+            toolbox.print.info('pwcli - Photowall CLI');
+            toolbox.print.info('');
+            toolbox.print.info('Run "pwcli" to start the interactive menu.');
+            toolbox.print.info('');
+            toolbox.print.info(
+              'For detailed help, see docs/help.md in the repository.',
+            );
+          }
+        } catch (error) {
+          toolbox.print.error(
+            'Error loading help documentation: ' + error.message,
+          );
+          toolbox.print.info('');
+          toolbox.print.info('Run "pwcli" to start the interactive menu.');
+        }
       },
     }) // provides default for help, h, --help, -h
     // .version() // provides default for version, v, --version, -v