diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index 3e06628..99c1bd3 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -80,6 +80,36 @@ type Command struct {
 	Subcommands map[string]*Command
 }
 
+// CommandSchema is a JSON-serializable representation of a command for LLM parsing
+type CommandSchema struct {
+	Name        string                    `json:"name"`
+	Description string                    `json:"description"`
+	Usage       string                    `json:"usage,omitempty"`
+	Subcommands map[string]*CommandSchema `json:"subcommands,omitempty"`
+}
+
+// toSchema converts a Command to its JSON-serializable schema
+func (cmd *Command) toSchema() *CommandSchema {
+	schema := &CommandSchema{
+		Name:        cmd.Name,
+		Description: cmd.Description,
+		Usage:       cmd.Usage,
+	}
+
+	if len(cmd.Subcommands) > 0 {
+		schema.Subcommands = make(map[string]*CommandSchema)
+		for name, subcmd := range cmd.Subcommands {
+			// Skip internal commands (prefixed with _)
+			if strings.HasPrefix(name, "_") {
+				continue
+			}
+			schema.Subcommands[name] = subcmd.toSchema()
+		}
+	}
+
+	return schema
+}
+
 // CLI manages the command-line interface
 type CLI struct {
 	rootCmd       *Command
@@ -203,7 +233,7 @@ func sanitizeTmuxSessionName(repoName string) string {
 // Execute executes the CLI with the given arguments
 func (c *CLI) Execute(args []string) error {
 	if len(args) == 0 {
-		return c.showHelp()
+		return c.showHelp(false)
 	}
 
 	// Check for --version or -v flag at top level
@@ -211,6 +241,18 @@ func (c *CLI) Execute(args []string) error {
 		return c.showVersion()
 	}
 
+	// Check for --help or -h with optional --json at top level
+	if args[0] == "--help" || args[0] == "-h" {
+		flags, _ := ParseFlags(args)
+		outputJSON := flags["json"] == "true"
+		return c.showHelp(outputJSON)
+	}
+
+	// Check for --json alone (output full command tree)
+	if args[0] == "--json" {
+		return c.showHelp(true)
+	}
+
 	return c.executeCommand(c.rootCmd, args)
 }
 
@@ -248,12 +290,19 @@ func (c *CLI) executeCommand(cmd *Command, args []string) error {
 		if cmd.Run != nil {
 			return cmd.Run([]string{})
 		}
-		return c.showCommandHelp(cmd)
+		return c.showCommandHelp(cmd, false)
 	}
 
-	// Check for --help or -h flag
+	// Check for --help or -h flag with optional --json
 	if args[0] == "--help" || args[0] == "-h" {
-		return c.showCommandHelp(cmd)
+		flags, _ := ParseFlags(args)
+		outputJSON := flags["json"] == "true"
+		return c.showCommandHelp(cmd, outputJSON)
+	}
+
+	// Check for --json alone (output command schema)
+	if args[0] == "--json" {
+		return c.showCommandHelp(cmd, true)
 	}
 
 	// Check for subcommands
@@ -270,7 +319,14 @@ func (c *CLI) executeCommand(cmd *Command, args []string) error {
 }
 
 // showHelp shows the main help message
-func (c *CLI) showHelp() error {
+func (c *CLI) showHelp(outputJSON bool) error {
+	if outputJSON {
+		schema := c.rootCmd.toSchema()
+		encoder := json.NewEncoder(os.Stdout)
+		encoder.SetIndent("", "  ")
+		return encoder.Encode(schema)
+	}
+
 	fmt.Println("multiclaude - repo-centric orchestrator for Claude Code")
 	fmt.Println()
 	fmt.Println("Usage: multiclaude <command> [options]")
@@ -283,11 +339,19 @@ func (c *CLI) showHelp() error {
 
 	fmt.Println()
 	fmt.Println("Use 'multiclaude <command> --help' for more information about a command.")
+	fmt.Println("Use 'multiclaude --json' for machine-readable command tree (LLM-friendly).")
 	return nil
 }
 
 // showCommandHelp shows help for a specific command
-func (c *CLI) showCommandHelp(cmd *Command) error {
+func (c *CLI) showCommandHelp(cmd *Command, outputJSON bool) error {
+	if outputJSON {
+		schema := cmd.toSchema()
+		encoder := json.NewEncoder(os.Stdout)
+		encoder.SetIndent("", "  ")
+		return encoder.Encode(schema)
+	}
+
 	fmt.Printf("%s - %s\n", cmd.Name, cmd.Description)
 	fmt.Println()
 	if cmd.Usage != "" {
diff --git a/internal/cli/cli_test.go b/internal/cli/cli_test.go
index 498577d..ea54f42 100644
--- a/internal/cli/cli_test.go
+++ b/internal/cli/cli_test.go
@@ -2811,6 +2811,69 @@ func TestVersionCommandJSON(t *testing.T) {
 	}
 }
 
+func TestHelpJSON(t *testing.T) {
+	cli, _, cleanup := setupTestEnvironment(t)
+	defer cleanup()
+
+	// Test --json flag at root level
+	err := cli.Execute([]string{"--json"})
+	if err != nil {
+		t.Errorf("Execute(--json) failed: %v", err)
+	}
+
+	// Test --help --json combination
+	err = cli.Execute([]string{"--help", "--json"})
+	if err != nil {
+		t.Errorf("Execute(--help --json) failed: %v", err)
+	}
+
+	// Test subcommand --json
+	err = cli.Execute([]string{"agent", "--json"})
+	if err != nil {
+		t.Errorf("Execute(agent --json) failed: %v", err)
+	}
+}
+
+func TestCommandSchemaConversion(t *testing.T) {
+	cmd := &Command{
+		Name:        "test",
+		Description: "test command",
+		Usage:       "multiclaude test [args]",
+		Subcommands: map[string]*Command{
+			"sub": {
+				Name:        "sub",
+				Description: "subcommand",
+				Usage:       "multiclaude test sub",
+			},
+			"_internal": {
+				Name:        "_internal",
+				Description: "internal command",
+			},
+		},
+	}
+
+	schema := cmd.toSchema()
+
+	if schema.Name != "test" {
+		t.Errorf("expected name 'test', got '%s'", schema.Name)
+	}
+	if schema.Description != "test command" {
+		t.Errorf("expected description 'test command', got '%s'", schema.Description)
+	}
+	if schema.Usage != "multiclaude test [args]" {
+		t.Errorf("expected usage 'multiclaude test [args]', got '%s'", schema.Usage)
+	}
+	if len(schema.Subcommands) != 1 {
+		t.Errorf("expected 1 subcommand (internal should be filtered), got %d", len(schema.Subcommands))
+	}
+	if _, exists := schema.Subcommands["sub"]; !exists {
+		t.Error("expected 'sub' subcommand to exist")
+	}
+	if _, exists := schema.Subcommands["_internal"]; exists {
+		t.Error("internal commands should be filtered from schema")
+	}
+}
+
 func TestShowHelpNoPanic(t *testing.T) {
 	cli, _, cleanup := setupTestEnvironment(t)
 	defer cleanup()
@@ -2822,7 +2885,7 @@ func TestShowHelpNoPanic(t *testing.T) {
 		}
 	}()
 
-	cli.showHelp()
+	cli.showHelp(false)
 }
 
 func TestExecuteEmptyArgs(t *testing.T) {