diff --git a/cli.py b/cli.py
index a2a3f8c17..0d13d230c 100755
--- a/cli.py
+++ b/cli.py
@@ -1942,18 +1942,22 @@ class HermesCLI:
         )
     
     def show_help(self):
-        """Display help information."""
-        _cprint(f"\n{_BOLD}+{'-' * 50}+{_RST}")
-        _cprint(f"{_BOLD}|{' ' * 14}(^_^)? Available Commands{' ' * 10}|{_RST}")
-        _cprint(f"{_BOLD}+{'-' * 50}+{_RST}\n")
-        
-        for cmd, desc in COMMANDS.items():
-            _cprint(f"  {_GOLD}{cmd:<15}{_RST} {_DIM}-{_RST} {desc}")
-        
+        """Display help information with categorized commands."""
+        from hermes_cli.commands import COMMANDS_BY_CATEGORY
+
+        _cprint(f"\n{_BOLD}+{'-' * 55}+{_RST}")
+        _cprint(f"{_BOLD}|{' ' * 14}(^_^)? Available Commands{' ' * 15}|{_RST}")
+        _cprint(f"{_BOLD}+{'-' * 55}+{_RST}")
+
+        for category, commands in COMMANDS_BY_CATEGORY.items():
+            _cprint(f"\n  {_BOLD}── {category} ──{_RST}")
+            for cmd, desc in commands.items():
+                _cprint(f"    {_GOLD}{cmd:<15}{_RST} {_DIM}-{_RST} {desc}")
+
         if _skill_commands:
             _cprint(f"\n  ⚡ {_BOLD}Skill Commands{_RST} ({len(_skill_commands)} installed):")
             for cmd, info in sorted(_skill_commands.items()):
-                _cprint(f"  {_GOLD}{cmd:<22}{_RST} {_DIM}-{_RST} {info['description']}")
+                _cprint(f"    {_GOLD}{cmd:<22}{_RST} {_DIM}-{_RST} {info['description']}")
 
         _cprint(f"\n  {_DIM}Tip: Just type your message to chat with Hermes!{_RST}")
         _cprint(f"  {_DIM}Multi-line: Alt+Enter for a new line{_RST}")
diff --git a/hermes_cli/commands.py b/hermes_cli/commands.py
index 72c9e77c1..e1b23d872 100644
--- a/hermes_cli/commands.py
+++ b/hermes_cli/commands.py
@@ -13,37 +13,43 @@ from typing import Any
 from prompt_toolkit.completion import Completer, Completion
 
 
-COMMANDS = {
-    "/help": "Show this help message",
-    "/tools": "List available tools",
-    "/toolsets": "List available toolsets",
-    "/model": "Show or change the current model",
-    "/provider": "Show available providers and current provider",
-    "/prompt": "View/set custom system prompt",
-    "/personality": "Set a predefined personality",
-    "/clear": "Clear screen and reset conversation (fresh start)",
-    "/history": "Show conversation history",
-    "/new": "Start a new conversation (reset history)",
-    "/reset": "Reset conversation only (keep screen)",
-    "/retry": "Retry the last message (resend to agent)",
-    "/undo": "Remove the last user/assistant exchange",
-    "/save": "Save the current conversation",
-    "/config": "Show current configuration",
-    "/cron": "Manage scheduled tasks (list, add, remove)",
-    "/skills": "Search, install, inspect, or manage skills from online registries",
-    "/platforms": "Show gateway/messaging platform status",
-    "/verbose": "Cycle tool progress display: off → new → all → verbose",
-    "/compress": "Manually compress conversation context (flush memories + summarize)",
-    "/title": "Set a title for the current session (usage: /title My Session Name)",
-    "/usage": "Show token usage for the current session",
-    "/insights": "Show usage insights and analytics (last 30 days)",
-    "/paste": "Check clipboard for an image and attach it",
-    "/reload-mcp": "Reload MCP servers from config.yaml",
-    "/rollback": "List or restore filesystem checkpoints (usage: /rollback [number])",
-    "/skin": "Show or change the display skin/theme",
-    "/quit": "Exit the CLI (also: /exit, /q)",
+# Commands organized by category for better help display
+COMMANDS_BY_CATEGORY = {
+    "Session": {
+        "/new": "Start a new conversation (reset history)",
+        "/reset": "Reset conversation only (keep screen)",
+        "/clear": "Clear screen and reset conversation (fresh start)",
+        "/history": "Show conversation history",
+        "/save": "Save the current conversation",
+        "/retry": "Retry the last message (resend to agent)",
+        "/undo": "Remove the last user/assistant exchange",
+    },
+    "Configuration": {
+        "/config": "Show current configuration",
+        "/model": "Show or change the current model",
+        "/prompt": "View/set custom system prompt",
+        "/personality": "Set a predefined personality",
+    },
+    "Tools & Skills": {
+        "/tools": "List available tools",
+        "/toolsets": "List available toolsets",
+        "/skills": "Search, install, inspect, or manage skills",
+        "/cron": "Manage scheduled tasks (list, add, remove)",
+    },
+    "Info": {
+        "/help": "Show this help message",
+        "/platforms": "Show gateway/messaging platform status",
+    },
+    "Exit": {
+        "/quit": "Exit the CLI (also: /exit, /q)",
+    },
 }
 
+# Flat dict for backwards compatibility and autocomplete
+COMMANDS = {}
+for category_commands in COMMANDS_BY_CATEGORY.values():
+    COMMANDS.update(category_commands)
+
 
 class SlashCommandCompleter(Completer):
     """Autocomplete for built-in slash commands and optional skill commands."""