diff --git a/Cargo.lock b/Cargo.lock
index 09c665d4..025aafb2 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1221,6 +1221,27 @@ version = "0.8.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e9b18233253483ce2f65329a24072ec414db782531bdbb7d0bbc4bd2ce6b7e21"
 
+[[package]]
+name = "color-print"
+version = "0.3.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3aa954171903797d5623e047d9ab69d91b493657917bdfb8c2c80ecaf9cdb6f4"
+dependencies = [
+ "color-print-proc-macro",
+]
+
+[[package]]
+name = "color-print-proc-macro"
+version = "0.3.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "692186b5ebe54007e45a59aea47ece9eb4108e141326c304cdc91699a7118a22"
+dependencies = [
+ "nom 7.1.3",
+ "proc-macro2",
+ "quote",
+ "syn 2.0.114",
+]
+
 [[package]]
 name = "color_quant"
 version = "1.1.0"
@@ -1525,6 +1546,7 @@ dependencies = [
  "clap",
  "clap_complete",
  "clap_mangen",
+ "color-print",
  "cortex-app-server",
  "cortex-common",
  "cortex-engine",
diff --git a/cortex-cli/Cargo.toml b/cortex-cli/Cargo.toml
index d01efa0c..72444c7d 100644
--- a/cortex-cli/Cargo.toml
+++ b/cortex-cli/Cargo.toml
@@ -39,6 +39,9 @@ cortex-share = { path = "../cortex-share" }
 clap = { workspace = true }
 clap_complete = { workspace = true }
 clap_mangen = { workspace = true }
+
+# For colored help output
+color-print = "0.3"
 tokio = { workspace = true, features = ["full"] }
 anyhow = { workspace = true }
 tracing = { workspace = true }
diff --git a/cortex-cli/src/main.rs b/cortex-cli/src/main.rs
index 9fd9098b..073dac22 100644
--- a/cortex-cli/src/main.rs
+++ b/cortex-cli/src/main.rs
@@ -10,11 +10,32 @@
 //! - Shell completions
 
 use anyhow::{Result, bail};
+use clap::builder::styling::{AnsiColor, Effects, Styles};
 use clap::{Args, CommandFactory, Parser, Subcommand};
 use clap_complete::{Shell, generate};
 use std::io;
 use std::path::PathBuf;
 
+/// Cortex CLI styled help theme.
+/// Uses a modern color scheme with cyan accents for a beautiful terminal experience.
+fn get_styles() -> Styles {
+    Styles::styled()
+        // Headers (USAGE, COMMANDS, OPTIONS) - Bold cyan
+        .header(AnsiColor::Cyan.on_default() | Effects::BOLD)
+        // Usage line - Green
+        .usage(AnsiColor::Green.on_default() | Effects::BOLD)
+        // Literals (command names, flag names) - Bold green
+        .literal(AnsiColor::Green.on_default() | Effects::BOLD)
+        // Placeholders (<VALUE>, [ARGS]) - Yellow
+        .placeholder(AnsiColor::Yellow.on_default())
+        // Errors - Bold red
+        .error(AnsiColor::Red.on_default() | Effects::BOLD)
+        // Valid values - Cyan
+        .valid(AnsiColor::Cyan.on_default())
+        // Invalid values - Yellow
+        .invalid(AnsiColor::Yellow.on_default())
+}
+
 use cortex_cli::acp_cmd::AcpCli;
 use cortex_cli::agent_cmd::AgentCli;
 use cortex_cli::debug_cmd::DebugCli;
@@ -82,29 +103,48 @@ impl LogLevel {
 }
 
 /// After-help section with environment variables documentation.
-const AFTER_HELP: &str = "\
-ENVIRONMENT VARIABLES:
-    CORTEX_HOME          Override config directory (default: ~/.config/cortex)
-    CORTEX_API_KEY       API key (alternative to --with-api-key)
-    CORTEX_MODEL         Default model (alternative to --model)
-    CORTEX_LOG_LEVEL     Log verbosity (error, warn, info, debug, trace)
-    NO_COLOR             Disable colored output (set to '1' or 'true')
-    VISUAL               Editor for /edit command (fallback: EDITOR)
-    EDITOR               Fallback editor if VISUAL is not set
-
-CONFIGURATION:
-    Config file: ~/.config/cortex/config.toml
-    Sessions:    ~/.local/share/cortex/sessions/
-    Logs:        ~/.cache/cortex/logs/
-    Agents:      ~/.cortex/agents/ (personal), .cortex/agents/ (project)
-
-EXAMPLES:
-    cortex                         Start interactive TUI
-    cortex \"fix the bug\"          Start TUI with initial prompt
-    cortex run \"explain this\"     Non-interactive single request
-    cortex exec \"run tests\"       Headless execution for CI/CD
-    cortex resume --last           Continue most recent session
-";
+const AFTER_HELP: &str = color_print::cstr!(
+    r#"
+<cyan,bold>ENVIRONMENT VARIABLES:</>
+    <green,bold>CORTEX_HOME</>          Override config directory (default: ~/.config/cortex)
+    <green,bold>CORTEX_API_KEY</>       API key (alternative to --with-api-key)
+    <green,bold>CORTEX_MODEL</>         Default model (alternative to --model)
+    <green,bold>CORTEX_LOG_LEVEL</>     Log verbosity (error, warn, info, debug, trace)
+    <green,bold>NO_COLOR</>             Disable colored output (set to '1' or 'true')
+    <green,bold>VISUAL</>               Editor for /edit command (fallback: EDITOR)
+    <green,bold>EDITOR</>               Fallback editor if VISUAL is not set
+
+<cyan,bold>PATHS:</>
+    <green,bold>Config file</>   ~/.config/cortex/config.toml
+    <green,bold>Sessions</>      ~/.local/share/cortex/sessions/
+    <green,bold>Logs</>          ~/.cache/cortex/logs/
+    <green,bold>Agents</>        ~/.cortex/agents/ (personal), .cortex/agents/ (project)
+
+<cyan,bold>QUICK START:</>
+    <yellow>cortex</>                         Start interactive TUI
+    <yellow>cortex</> <dim>"fix the bug"</>          Start TUI with initial prompt
+    <yellow>cortex run</> <dim>"explain this"</>     Non-interactive single request
+    <yellow>cortex exec</> <dim>"run tests"</>       Headless execution for CI/CD
+    <yellow>cortex resume --last</>           Continue most recent session
+
+<cyan,bold>LEARN MORE:</>
+    Documentation:   <blue,underline>https://docs.cortex.foundation</>
+    Report issues:   <blue,underline>https://github.com/CortexLM/cortex-cli/issues</>
+"#
+);
+
+/// Before-help section with ASCII art banner.
+const BEFORE_HELP: &str = color_print::cstr!(
+    r#"
+<cyan,bold>   ██████╗ ██████╗ ██████╗ ████████╗███████╗██╗  ██╗</>
+<cyan,bold>  ██╔════╝██╔═══██╗██╔══██╗╚══██╔══╝██╔════╝╚██╗██╔╝</>
+<cyan,bold>  ██║     ██║   ██║██████╔╝   ██║   █████╗   ╚███╔╝ </>
+<cyan,bold>  ██║     ██║   ██║██╔══██╗   ██║   ██╔══╝   ██╔██╗ </>
+<cyan,bold>  ╚██████╗╚██████╔╝██║  ██║   ██║   ███████╗██╔╝ ██╗</>
+<cyan,bold>   ╚═════╝ ╚═════╝ ╚═╝  ╚═╝   ╚═╝   ╚══════╝╚═╝  ╚═╝</>
+<dim>                 AI-Powered Coding Agent</>
+"#
+);
 
 /// Cortex CLI - AI Coding Agent
 ///
@@ -114,8 +154,10 @@ EXAMPLES:
 #[command(author, version)]
 #[command(about = "Cortex - AI Coding Agent", long_about = None)]
 #[command(
+    styles = get_styles(),
     subcommand_negates_reqs = true,
     override_usage = "cortex [OPTIONS] [PROMPT]\n       cortex [OPTIONS] <COMMAND> [ARGS]",
+    before_help = BEFORE_HELP,
     after_help = AFTER_HELP
 )]
 struct Cli {
@@ -132,8 +174,11 @@ struct Cli {
 /// Arguments for interactive mode.
 #[derive(Args, Debug, Default)]
 struct InteractiveArgs {
-    /// Model to use
-    #[arg(short, long)]
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Model Configuration
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// Model to use (e.g., claude-sonnet-4-20250514, gpt-4o, gemini-2.0-flash)
+    #[arg(short, long, help_heading = "Model Configuration")]
     model: Option<String>,
 
     /// Use open-source/local LLM providers instead of cloud APIs.
@@ -143,15 +188,22 @@ struct InteractiveArgs {
     ///   llamacpp   - llama.cpp server
     ///   vllm       - vLLM inference server
     ///   openrouter - OpenRouter API (cloud, supports many OSS models)
-    #[arg(long = "oss", default_value_t = false)]
+    #[arg(
+        long = "oss",
+        default_value_t = false,
+        help_heading = "Model Configuration"
+    )]
     oss: bool,
 
     /// Configuration profile from config.toml
-    #[arg(long = "profile", short = 'p')]
+    #[arg(long = "profile", short = 'p', help_heading = "Model Configuration")]
     config_profile: Option<String>,
 
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Security & Sandbox
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Select the sandbox policy for shell commands
-    #[arg(long = "sandbox", short = 's')]
+    #[arg(long = "sandbox", short = 's', help_heading = "Security")]
     sandbox_mode: Option<String>,
 
     /// Set the approval policy for tool executions.
@@ -160,7 +212,12 @@ struct InteractiveArgs {
     ///   medium - Ask for approval only for risky operations
     ///   low    - Rarely ask for approval (only for dangerous operations)
     ///   yolo   - Never ask for approval (DANGEROUS: use with caution)
-    #[arg(long = "ask-for-approval", short = 'a', value_name = "POLICY")]
+    #[arg(
+        long = "ask-for-approval",
+        short = 'a',
+        value_name = "POLICY",
+        help_heading = "Security"
+    )]
     approval_policy: Option<String>,
 
     /// Enable fully automatic mode with sandboxed execution.
@@ -168,7 +225,7 @@ struct InteractiveArgs {
     /// The sandbox ensures operations are confined to the workspace directory.
     /// Best suited for automated CI/CD pipelines and non-destructive scripted workflows.
     /// For interactive use, consider --ask-for-approval=medium instead.
-    #[arg(long = "full-auto", default_value_t = false)]
+    #[arg(long = "full-auto", default_value_t = false, help_heading = "Security")]
     full_auto: bool,
 
     /// Skip all confirmation prompts and execute commands without sandboxing. DANGEROUS!
@@ -176,14 +233,34 @@ struct InteractiveArgs {
         long = "dangerously-bypass-approvals-and-sandbox",
         alias = "yolo",
         default_value_t = false,
-        conflicts_with_all = ["approval_policy", "full_auto"]
+        conflicts_with_all = ["approval_policy", "full_auto"],
+        help_heading = "Security"
     )]
     dangerously_bypass_approvals_and_sandbox: bool,
 
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Workspace & Files
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Tell the agent to use the specified directory as its working root
-    #[arg(long = "cd", short = 'C', value_name = "DIR")]
+    #[arg(
+        long = "cd",
+        short = 'C',
+        value_name = "DIR",
+        help_heading = "Workspace"
+    )]
     cwd: Option<PathBuf>,
 
+    /// Additional directories that should be writable
+    #[arg(long = "add-dir", value_name = "DIR", help_heading = "Workspace")]
+    add_dir: Vec<PathBuf>,
+
+    /// Image files to attach to the initial prompt
+    #[arg(long = "image", short = 'i', value_delimiter = ',', num_args = 1.., help_heading = "Workspace")]
+    images: Vec<PathBuf>,
+
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Features
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Enable web search capability for the agent.
     /// When enabled, the agent can:
     ///   - Search the web for up-to-date information and documentation
@@ -191,20 +268,21 @@ struct InteractiveArgs {
     ///   - Look up library/API documentation
     ///   - Research error messages and solutions
     /// Requires network access. Search results are automatically filtered for relevance.
-    #[arg(long = "search", default_value_t = false)]
+    #[arg(long = "search", default_value_t = false, help_heading = "Features")]
     web_search: bool,
 
-    /// Additional directories that should be writable
-    #[arg(long = "add-dir", value_name = "DIR")]
-    add_dir: Vec<PathBuf>,
-
-    /// Image files to attach to the initial prompt
-    #[arg(long = "image", short = 'i', value_delimiter = ',', num_args = 1..)]
-    images: Vec<PathBuf>,
-
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Debugging & Output
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Set log verbosity level (error, warn, info, debug, trace)
     /// Can also be set via CORTEX_LOG_LEVEL environment variable
-    #[arg(long = "log-level", short = 'L', value_enum, default_value = "info")]
+    #[arg(
+        long = "log-level",
+        short = 'L',
+        value_enum,
+        default_value = "info",
+        help_heading = "Debugging"
+    )]
     log_level: LogLevel,
 
     /// Enable debug logging (deprecated: use --log-level debug instead)
@@ -216,91 +294,167 @@ struct InteractiveArgs {
     prompt: Vec<String>,
 }
 
+// Command category display names for styled help output
+const CAT_EXECUTION: &str = "Execution Modes";
+const CAT_SESSION: &str = "Session Management";
+const CAT_AUTH: &str = "Authentication";
+const CAT_EXTENSION: &str = "Extensibility";
+const CAT_CONFIG: &str = "Configuration";
+const CAT_UTILITIES: &str = "Utilities";
+const CAT_ADVANCED: &str = "Advanced";
+
 #[derive(Subcommand)]
 enum Commands {
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Execution Modes
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Run Cortex non-interactively with advanced options
-    #[command(visible_alias = "r")]
+    #[command(visible_alias = "r", display_order = 1)]
+    #[command(next_help_heading = CAT_EXECUTION)]
     Run(RunCli),
 
-    /// Execute a single command in non-interactive (headless) mode.
-    /// Designed for CI/CD pipelines, shell scripts, and batch processing.
-    /// Supports autonomy levels (--auto), output formats, and multi-turn conversations.
-    #[command(visible_alias = "e")]
+    /// Execute in headless mode (for CI/CD, scripts, automation)
+    #[command(visible_alias = "e", display_order = 2)]
+    #[command(next_help_heading = CAT_EXECUTION)]
     Exec(ExecCli),
 
-    /// Manage login
-    Login(LoginCommand),
-
-    /// Remove stored authentication credentials
-    Logout(LogoutCommand),
-
-    /// Manage MCP servers
-    Mcp(McpCli),
-
-    /// Manage agents (list, create, show)
-    Agent(AgentCli),
-
-    /// Run the MCP server (stdio transport)
-    McpServer,
-
-    /// Generate shell completion scripts
-    Completion(CompletionCommand),
-
-    /// Run commands within a Cortex-provided sandbox
-    #[command(visible_alias = "sb")]
-    Sandbox(SandboxArgs),
-
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Session Management
+    // ═══════════════════════════════════════════════════════════════════════════
     /// Resume a previous interactive session
+    #[command(display_order = 10)]
+    #[command(next_help_heading = CAT_SESSION)]
     Resume(ResumeCommand),
 
     /// List previous sessions
+    #[command(display_order = 11)]
+    #[command(next_help_heading = CAT_SESSION)]
     Sessions(SessionsCommand),
 
     /// Export a session to JSON format
+    #[command(display_order = 12)]
+    #[command(next_help_heading = CAT_SESSION)]
     Export(ExportCommand),
 
     /// Import a session from JSON file or URL
+    #[command(display_order = 13)]
+    #[command(next_help_heading = CAT_SESSION)]
     Import(ImportCommand),
 
-    /// Show configuration
-    Config(ConfigCommand),
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Authentication
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// Authenticate with Cortex API
+    #[command(display_order = 20)]
+    #[command(next_help_heading = CAT_AUTH)]
+    Login(LoginCommand),
 
-    /// Inspect feature flags
-    Features(FeaturesCommand),
+    /// Remove stored authentication credentials
+    #[command(display_order = 21)]
+    #[command(next_help_heading = CAT_AUTH)]
+    Logout(LogoutCommand),
 
-    /// Run the HTTP API server (for desktop/web integration)
-    Serve(ServeCommand),
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Extensibility (Agents, MCP, Plugins)
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// Manage agents (list, create, show)
+    #[command(display_order = 30)]
+    #[command(next_help_heading = CAT_EXTENSION)]
+    Agent(AgentCli),
 
-    /// List available models
-    Models(ModelsCli),
+    /// Manage MCP (Model Context Protocol) servers
+    #[command(display_order = 31)]
+    #[command(next_help_heading = CAT_EXTENSION)]
+    Mcp(McpCli),
 
-    /// Check for and install updates
-    Upgrade(UpgradeCli),
+    /// Run the MCP server (stdio transport)
+    #[command(display_order = 32, hide = true)]
+    #[command(next_help_heading = CAT_EXTENSION)]
+    McpServer,
 
-    /// Uninstall Cortex CLI
-    Uninstall(UninstallCli),
+    /// Start ACP server for IDE integration (e.g., Zed)
+    #[command(display_order = 33)]
+    #[command(next_help_heading = CAT_EXTENSION)]
+    Acp(AcpCli),
 
-    /// Show usage statistics
-    Stats(StatsCli),
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Configuration
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// Show or edit configuration
+    #[command(display_order = 40)]
+    #[command(next_help_heading = CAT_CONFIG)]
+    Config(ConfigCommand),
+
+    /// List available models
+    #[command(display_order = 41)]
+    #[command(next_help_heading = CAT_CONFIG)]
+    Models(ModelsCli),
+
+    /// Inspect feature flags
+    #[command(display_order = 42)]
+    #[command(next_help_heading = CAT_CONFIG)]
+    Features(FeaturesCommand),
 
-    /// GitHub Actions integration
-    #[command(visible_alias = "gh")]
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Utilities
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// GitHub integration (actions, workflows)
+    #[command(visible_alias = "gh", display_order = 50)]
+    #[command(next_help_heading = CAT_UTILITIES)]
     Github(GitHubCli),
 
     /// Checkout a pull request
+    #[command(display_order = 51)]
+    #[command(next_help_heading = CAT_UTILITIES)]
     Pr(PrCli),
 
     /// Scrape web content to markdown/text/html
+    #[command(display_order = 52)]
+    #[command(next_help_heading = CAT_UTILITIES)]
     Scrape(ScrapeCommand),
 
-    /// Start ACP server for IDE integration (e.g., Zed)
-    Acp(AcpCli),
+    /// Show usage statistics
+    #[command(display_order = 53)]
+    #[command(next_help_heading = CAT_UTILITIES)]
+    Stats(StatsCli),
 
-    /// Debug and diagnostic commands
-    Debug(DebugCli),
+    /// Generate shell completion scripts
+    #[command(display_order = 54)]
+    #[command(next_help_heading = CAT_UTILITIES)]
+    Completion(CompletionCommand),
+
+    // ═══════════════════════════════════════════════════════════════════════════
+    // Advanced
+    // ═══════════════════════════════════════════════════════════════════════════
+    /// Run commands within a Cortex-provided sandbox
+    #[command(visible_alias = "sb", display_order = 60)]
+    #[command(next_help_heading = CAT_ADVANCED)]
+    Sandbox(SandboxArgs),
+
+    /// Run the HTTP API server (for desktop/web integration)
+    #[command(display_order = 61)]
+    #[command(next_help_heading = CAT_ADVANCED)]
+    Serve(ServeCommand),
 
     /// Discover Cortex servers on the local network
+    #[command(display_order = 62)]
+    #[command(next_help_heading = CAT_ADVANCED)]
     Servers(ServersCommand),
+
+    /// Check for and install updates
+    #[command(display_order = 70)]
+    #[command(next_help_heading = CAT_ADVANCED)]
+    Upgrade(UpgradeCli),
+
+    /// Uninstall Cortex CLI
+    #[command(display_order = 71)]
+    #[command(next_help_heading = CAT_ADVANCED)]
+    Uninstall(UninstallCli),
+
+    /// Debug and diagnostic commands
+    #[command(display_order = 99)]
+    #[command(next_help_heading = CAT_ADVANCED)]
+    Debug(DebugCli),
 }
 
 // Note: ExecCommand has been replaced by the comprehensive ExecCli from exec_cmd module.