diff --git a/src/cli.ts b/src/cli.ts
index 2bd21b20..afb5d813 100644
--- a/src/cli.ts
+++ b/src/cli.ts
@@ -1,3 +1,12 @@
+/**
+ * @fileoverview Claudeman CLI command definitions
+ *
+ * Defines all CLI commands and subcommands for managing Claude sessions,
+ * tasks, Ralph loops, and the web server.
+ *
+ * @module cli
+ */
+
 import { Command } from 'commander';
 import chalk from 'chalk';
 import { getSessionManager } from './session-manager.js';
diff --git a/src/index.ts b/src/index.ts
index 8a19053a..afcb6528 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -1,4 +1,12 @@
 #!/usr/bin/env node
+/**
+ * @fileoverview Claudeman CLI entry point
+ *
+ * This is the main executable entry point for the Claudeman CLI.
+ * It sets up global error handlers and invokes the CLI parser.
+ *
+ * @module index
+ */
 
 import { program } from './cli.js';
 
diff --git a/src/templates/claude-md.ts b/src/templates/claude-md.ts
index 573fbe8a..5a6c4ea7 100644
--- a/src/templates/claude-md.ts
+++ b/src/templates/claude-md.ts
@@ -1,5 +1,26 @@
+/**
+ * @fileoverview CLAUDE.md template generation
+ *
+ * Generates CLAUDE.md configuration files for new Claudeman projects.
+ * Supports custom templates with placeholder substitution.
+ *
+ * @module templates/claude-md
+ */
+
 import { existsSync, readFileSync } from 'node:fs';
 
+/**
+ * Generates a CLAUDE.md configuration file for a new project.
+ *
+ * Supports custom templates via `templatePath`. If provided and the file exists,
+ * placeholders ([PROJECT_NAME], [PROJECT_DESCRIPTION], [DATE]) are replaced.
+ * Falls back to the default template if custom template is unavailable.
+ *
+ * @param caseName - The project/case name to use in the template
+ * @param description - Optional project description (defaults to "A new project")
+ * @param templatePath - Optional path to a custom template file
+ * @returns The generated CLAUDE.md content
+ */
 export function generateClaudeMd(caseName: string, description: string = '', templatePath?: string): string {
   const date = new Date().toISOString().split('T')[0];
 
diff --git a/src/web/server.ts b/src/web/server.ts
index 322b0700..b61c70a2 100644
--- a/src/web/server.ts
+++ b/src/web/server.ts
@@ -1,3 +1,15 @@
+/**
+ * @fileoverview Claudeman web server and REST API
+ *
+ * Provides a Fastify-based web server with:
+ * - REST API for session management, respawn control, and monitoring
+ * - Server-Sent Events (SSE) for real-time updates at /api/events
+ * - Static file serving for the web UI
+ * - 60fps terminal streaming with batched updates
+ *
+ * @module web/server
+ */
+
 import Fastify, { FastifyInstance, FastifyReply } from 'fastify';
 import fastifyStatic from '@fastify/static';
 import { join, dirname } from 'node:path';