diff --git a/README.md b/README.md
index 1720456..28857ab 100644
--- a/README.md
+++ b/README.md
@@ -76,6 +76,7 @@
 - 🤖 **whisper.cpp by default** - High-performance C++ speech recognition
 - 🎮 **Universal GPU support** - Vulkan acceleration for AMD, Intel, and NVIDIA
 - 🎨 **System tray integration** with visual status indicators
+- 🚀 **Start on login support** via XDG autostart (desktop-session startup)
 - 🔊 **Pleasant audio feedback** - smooth gliding tones, headphone-friendly
 - ⚙️ **Graphical settings** dialog for easy configuration
 - 📦 **3 engine choices** - whisper.cpp (default), OpenAI Whisper, or VOSK
@@ -239,8 +240,30 @@ vocalinux --engine whisper        # Use OpenAI Whisper engine
 vocalinux --engine vosk           # Use VOSK engine
 vocalinux --model medium          # Use medium-sized model
 vocalinux --wayland               # Force Wayland mode
+vocalinux --start-minimized       # Start without first-run modal prompts
 ```
 
+### Autostart on Login
+
+Vocalinux uses the Linux desktop standard for autostart:
+
+- **Mechanism**: XDG autostart desktop entry (`vocalinux.desktop`)
+- **Path**: `$XDG_CONFIG_HOME/autostart/` or `~/.config/autostart/` (fallback)
+- **Launch mode**: Starts as a regular **user desktop app** in your graphical session
+- **Not used**: No `systemd` unit/service is created by Vocalinux for autostart
+
+How to enable/disable:
+
+- First-run welcome dialog
+- Tray menu: **Start on Login**
+- Settings dialog: **Start on Login**
+
+Compatibility notes:
+
+- Works on mainstream desktop environments (GNOME, KDE, Xfce, Cinnamon, MATE, LXQt)
+- On minimal/custom window-manager sessions, an autostart handler may be required
+  (for example DE-specific startup hooks or tools like `dex`)
+
 ## ⚙️ Configuration
 
 Configuration is stored in `~/.config/vocalinux/config.json`:
@@ -301,6 +324,7 @@ vocalinux/
 - [Installation Guide](docs/INSTALL.md) - Detailed installation instructions
 - [Update Guide](docs/UPDATE.md) - How to update Vocalinux
 - [User Guide](docs/USER_GUIDE.md) - Complete user documentation
+- [Distribution Compatibility](docs/DISTRO_COMPATIBILITY.md) - Distro/session behavior and caveats
 - [Contributing](CONTRIBUTING.md) - Development setup and contribution guidelines
 
 ## 🔊 Sound Customization
diff --git a/docs/DISTRO_COMPATIBILITY.md b/docs/DISTRO_COMPATIBILITY.md
index ef7ffa2..4753a2f 100644
--- a/docs/DISTRO_COMPATIBILITY.md
+++ b/docs/DISTRO_COMPATIBILITY.md
@@ -204,6 +204,21 @@ For unsupported or experimental distributions:
 | i3 | ✅ Good Support | X11, uses xdotool |
 | Hyprland | ⚠️ Experimental | Wayland, may need wtype configuration |
 
+### Autostart Compatibility
+
+Vocalinux uses **XDG autostart desktop entries** for "Start on Login".
+
+- Desktop-session autostart file location:
+  - `$XDG_CONFIG_HOME/autostart/vocalinux.desktop`, or
+  - `~/.config/autostart/vocalinux.desktop` (fallback)
+- This launches Vocalinux as a user GUI app after login.
+- Vocalinux does **not** create a `systemd` service/unit for this feature.
+
+Practical caveat:
+
+- Mainstream desktop environments generally honor XDG autostart.
+- Minimal/custom WM sessions may need an explicit autostart manager or WM startup hook.
+
 ## Display Server
 
 | Display Server | Status | Notes |
diff --git a/docs/INSTALL.md b/docs/INSTALL.md
index 8e47b8e..0530cae 100644
--- a/docs/INSTALL.md
+++ b/docs/INSTALL.md
@@ -166,8 +166,21 @@ vocalinux --model small           # Use small model
 vocalinux --model medium          # Use medium model
 vocalinux --model large           # Use large model
 vocalinux --wayland               # Force Wayland compatibility mode
+vocalinux --start-minimized       # Start without first-run modal prompts
 ```
 
+## Autostart Approach
+
+Vocalinux autostart is implemented with **XDG Autostart** (desktop entry), not as a `systemd` background service.
+
+- Enabling **Start on Login** creates `vocalinux.desktop` in:
+  - `$XDG_CONFIG_HOME/autostart/`, or
+  - `~/.config/autostart/` (fallback)
+- The autostart entry launches Vocalinux as a normal user desktop app at login.
+- No `systemd --user` unit is created by Vocalinux for this feature.
+
+This keeps behavior aligned with standard Linux desktop sessions and avoids service/session environment mismatches for GUI apps.
+
 ## Directory Structure
 
 Vocalinux follows the [XDG Base Directory Specification](https://specifications.freedesktop.org/basedir-spec/basedir-spec-latest.html):
diff --git a/docs/USER_GUIDE.md b/docs/USER_GUIDE.md
index b04405a..9440c44 100644
--- a/docs/USER_GUIDE.md
+++ b/docs/USER_GUIDE.md
@@ -4,7 +4,27 @@ This guide explains how to use Vocalinux effectively.
 
 ## Getting Started
 
-After installing Vocalinux (see the [Installation Guide](INSTALL.md)), you can start the application from the terminal or add it to your startup applications.
+After installing Vocalinux (see the [Installation Guide](INSTALL.md)), you can start the application from the terminal and optionally enable start-on-login.
+
+## Start on Login (Autostart)
+
+Vocalinux supports login autostart using the standard Linux desktop-session mechanism.
+
+- **Where to enable it**:
+  - First-run welcome dialog
+  - Tray menu: **Start on Login**
+  - Settings dialog: **Start on Login**
+- **What Vocalinux creates**:
+  - `vocalinux.desktop` in `$XDG_CONFIG_HOME/autostart/` or `~/.config/autostart/`
+- **How it starts**:
+  - As a regular user GUI app in your desktop session (`--start-minimized`)
+- **What it does not do**:
+  - It does not create a `systemd` service/unit for autostart
+
+### Desktop Compatibility Notes
+
+- Works on most mainstream desktop environments (GNOME, KDE, Xfce, Cinnamon, MATE, LXQt)
+- On minimal/custom window managers, autostart may require an autostart manager or desktop-specific startup hook
 
 ## Basic Usage
 
diff --git a/install.sh b/install.sh
index d6fbac7..4855693 100755
--- a/install.sh
+++ b/install.sh
@@ -25,8 +25,33 @@ command_exists() {
     command -v "$1" >/dev/null 2>&1
 }
 
+get_vocalinux_pids() {
+    pgrep -f "vocalinux" 2>/dev/null | while read -r pid; do
+        [ -z "$pid" ] && continue
+
+        if [ "$pid" = "$$" ] || [ "$pid" = "$PPID" ]; then
+            continue
+        fi
+
+        local stat
+        stat=$(ps -o stat= -p "$pid" 2>/dev/null | awk '{print $1}')
+        if [[ "$stat" == Z* ]]; then
+            continue
+        fi
+
+        local cmd
+        cmd=$(ps -o args= -p "$pid" 2>/dev/null)
+        if [[ "$cmd" == *"install.sh"* ]] || [[ "$cmd" == *"uninstall.sh"* ]]; then
+            continue
+        fi
+
+        echo "$pid"
+    done
+}
+
 check_running_processes() {
-    local PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+    local PIDS
+    PIDS=$(get_vocalinux_pids || true)
     
     if [ -n "$PIDS" ]; then
         print_warning "Found running Vocalinux process(es): $PIDS"
@@ -48,7 +73,8 @@ check_running_processes() {
         echo "$PIDS" | xargs -r kill -TERM 2>/dev/null || true
         sleep 2
         
-        local REMAINING_PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+        local REMAINING_PIDS
+        REMAINING_PIDS=$(get_vocalinux_pids || true)
         
         if [ -n "$REMAINING_PIDS" ]; then
             print_warning "Some processes still running, forcing termination..."
@@ -56,7 +82,8 @@ check_running_processes() {
             sleep 1
         fi
         
-        local FINAL_PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+        local FINAL_PIDS
+        FINAL_PIDS=$(get_vocalinux_pids || true)
         if [ -n "$FINAL_PIDS" ]; then
             print_error "Could not terminate all Vocalinux processes: $FINAL_PIDS"
             print_error "Please manually kill these processes and run the installer again."
diff --git a/src/vocalinux/main.py b/src/vocalinux/main.py
index 31ebfce..589396b 100644
--- a/src/vocalinux/main.py
+++ b/src/vocalinux/main.py
@@ -61,6 +61,11 @@ def parse_arguments():
         help="Speech recognition engine to use (whisper_cpp recommended for best performance)",
     )
     parser.add_argument("--wayland", action="store_true", help="Force Wayland compatibility mode")
+    parser.add_argument(
+        "--start-minimized",
+        action="store_true",
+        help="Start minimized to system tray",
+    )
     return parser.parse_args()
 
 
@@ -159,6 +164,31 @@ def main():
     saved_settings = config_manager.get_settings().get("speech_recognition", {})
     audio_settings = config_manager.get_settings().get("audio", {})
 
+    general_settings = config_manager.get_settings().get("general", {})
+    first_run = general_settings.get("first_run", True)
+    should_prompt_first_run = first_run and not args.start_minimized
+
+    if should_prompt_first_run:
+        from .ui.first_run_dialog import show_first_run_dialog
+
+        result = show_first_run_dialog()
+        if result == "yes":
+            from .ui import autostart_manager
+
+            if autostart_manager.set_autostart(True):
+                config_manager.set("general", "autostart", True)
+            else:
+                config_manager.set("general", "autostart", False)
+        elif result == "no":
+            from .ui import autostart_manager
+
+            autostart_manager.set_autostart(False)
+            config_manager.set("general", "autostart", False)
+
+        if result in {"yes", "no"}:
+            config_manager.set("general", "first_run", False)
+            config_manager.save_settings()
+
     # CLI arguments take precedence over saved config
     # We need to check if the user explicitly provided arguments
     # by examining sys.argv since argparse defaults don't tell us this
diff --git a/src/vocalinux/ui/autostart_manager.py b/src/vocalinux/ui/autostart_manager.py
new file mode 100644
index 0000000..261f90c
--- /dev/null
+++ b/src/vocalinux/ui/autostart_manager.py
@@ -0,0 +1,98 @@
+"""
+Autostart manager for Vocalinux.
+
+This module handles the creation and removal of the XDG autostart desktop entry
+for automatically starting Vocalinux on login.
+"""
+
+import logging
+import os
+import shlex
+import shutil
+import sys
+from pathlib import Path
+
+logger = logging.getLogger(__name__)
+
+DESKTOP_FILENAME = "vocalinux.desktop"
+
+
+def get_autostart_dir() -> Path:
+    xdg_config_home = os.environ.get("XDG_CONFIG_HOME")
+    if xdg_config_home:
+        return Path(xdg_config_home).expanduser() / "autostart"
+    return Path.home() / ".config" / "autostart"
+
+
+def get_autostart_file() -> Path:
+    return get_autostart_dir() / DESKTOP_FILENAME
+
+
+def get_exec_command() -> str:
+    installed_command = shutil.which("vocalinux")
+    if installed_command:
+        return f"{shlex.quote(installed_command)} --start-minimized"
+
+    if getattr(sys, "frozen", False):
+        return f"{shlex.quote(sys.executable)} --start-minimized"
+
+    return f"{shlex.quote(sys.executable)} -m vocalinux.main --start-minimized"
+
+
+def is_autostart_enabled() -> bool:
+    """Check if autostart is currently enabled."""
+    return get_autostart_file().exists()
+
+
+def enable_autostart() -> bool:
+    """Enable autostart by creating the desktop entry file."""
+    try:
+        autostart_dir = get_autostart_dir()
+        autostart_file = get_autostart_file()
+        autostart_dir.mkdir(parents=True, exist_ok=True)
+
+        exec_command = get_exec_command()
+        logger.info(f"Creating autostart entry with command: {exec_command}")
+
+        desktop_entry = f"""[Desktop Entry]
+Version=1.0
+Type=Application
+Name=Vocalinux
+Exec={exec_command}
+Icon=vocalinux
+Comment=Voice dictation for Linux
+Terminal=false
+StartupNotify=false
+X-GNOME-Autostart-enabled=true
+"""
+
+        with open(autostart_file, "w", encoding="utf-8") as f:
+            f.write(desktop_entry)
+
+        logger.info(f"Autostart enabled: {autostart_file}")
+        return True
+
+    except Exception as e:
+        logger.error(f"Failed to enable autostart: {e}")
+        return False
+
+
+def disable_autostart() -> bool:
+    """Disable autostart by removing the desktop entry file."""
+    try:
+        autostart_file = get_autostart_file()
+        if autostart_file.exists():
+            autostart_file.unlink()
+            logger.info(f"Autostart disabled: {autostart_file}")
+        return True
+
+    except Exception as e:
+        logger.error(f"Failed to disable autostart: {e}")
+        return False
+
+
+def set_autostart(enabled: bool) -> bool:
+    """Set autostart enabled or disabled."""
+    if enabled:
+        return enable_autostart()
+    return disable_autostart()
diff --git a/src/vocalinux/ui/config_manager.py b/src/vocalinux/ui/config_manager.py
index da155b3..408f42c 100644
--- a/src/vocalinux/ui/config_manager.py
+++ b/src/vocalinux/ui/config_manager.py
@@ -40,6 +40,10 @@ DEFAULT_CONFIG = {
         "start_minimized": False,
         "show_notifications": True,
     },
+    "general": {
+        "autostart": False,
+        "first_run": True,
+    },
     "advanced": {
         "debug_logging": False,
         "wayland_mode": False,
diff --git a/src/vocalinux/ui/first_run_dialog.py b/src/vocalinux/ui/first_run_dialog.py
new file mode 100644
index 0000000..f6bf83a
--- /dev/null
+++ b/src/vocalinux/ui/first_run_dialog.py
@@ -0,0 +1,121 @@
+"""
+First-run dialog for Vocalinux.
+
+This module shows a dialog on first run to ask the user about autostart preferences.
+"""
+
+import logging
+from typing import Optional
+
+import gi
+
+gi.require_version("Gtk", "3.0")
+from gi.repository import Gtk
+
+logger = logging.getLogger(__name__)
+
+
+class FirstRunDialog(Gtk.Dialog):
+    """Dialog shown on first run to configure autostart preference."""
+
+    def __init__(self, parent: Optional[Gtk.Window] = None):
+        super().__init__(
+            title="Welcome to Vocalinux",
+            transient_for=parent,
+            flags=Gtk.DialogFlags.MODAL,
+        )
+        self.set_default_size(440, 280)
+
+        box = self.get_content_area()
+        box.set_spacing(16)
+        box.set_margin_start(24)
+        box.set_margin_end(24)
+        box.set_margin_top(24)
+        box.set_margin_bottom(20)
+
+        title_label = Gtk.Label(label="<b>Welcome to Vocalinux!</b>", use_markup=True)
+        title_label.set_justify(Gtk.Justification.CENTER)
+        box.pack_start(title_label, False, False, 0)
+
+        description_label = Gtk.Label(
+            label="Vocalinux runs from your system tray so you can start and stop voice typing anytime.",
+            wrap=True,
+            justify=Gtk.Justification.CENTER,
+        )
+        box.pack_start(description_label, False, False, 8)
+
+        quick_guide_label = Gtk.Label(
+            label=(
+                "<b>Quick start</b>\n"
+                "1. Open the tray icon and choose Start Voice Typing\n"
+                "2. Open Settings from the tray menu to configure shortcuts, model, and audio"
+            ),
+            use_markup=True,
+            wrap=True,
+            justify=Gtk.Justification.LEFT,
+            xalign=0,
+        )
+        box.pack_start(quick_guide_label, False, False, 0)
+
+        subtitle_label = Gtk.Label(
+            label="Would you like Vocalinux to start automatically when you log in?",
+            wrap=True,
+            justify=Gtk.Justification.CENTER,
+        )
+        subtitle_label.get_style_context().add_class("preference-row-subtitle")
+        box.pack_start(subtitle_label, False, False, 0)
+
+        button_box = Gtk.Box(orientation=Gtk.Orientation.HORIZONTAL, spacing=8)
+        button_box.set_halign(Gtk.Align.CENTER)
+        button_box.set_margin_top(16)
+
+        yes_button = Gtk.Button(label="Yes, start on login")
+        yes_button.get_style_context().add_class("suggested-action")
+        yes_button.connect("clicked", self._on_yes_clicked)
+        button_box.pack_start(yes_button, False, False, 0)
+
+        no_button = Gtk.Button(label="No, I'll start manually")
+        no_button.connect("clicked", self._on_no_clicked)
+        button_box.pack_start(no_button, False, False, 0)
+
+        later_button = Gtk.Button(label="Ask me later")
+        later_button.connect("clicked", self._on_later_clicked)
+        button_box.pack_start(later_button, False, False, 0)
+
+        box.pack_start(button_box, False, False, 0)
+
+        self.result = None
+        self.show_all()
+
+    def _on_yes_clicked(self, widget):
+        """Handle Yes button click."""
+        self.result = "yes"
+        self.destroy()
+
+    def _on_no_clicked(self, widget):
+        """Handle No button click."""
+        self.result = "no"
+        self.destroy()
+
+    def _on_later_clicked(self, widget):
+        """Handle Later button click."""
+        self.result = "later"
+        self.destroy()
+
+
+def show_first_run_dialog(parent: Optional[Gtk.Window] = None) -> Optional[str]:
+    """
+    Show the first-run dialog and return the user's choice.
+
+    Args:
+        parent: The parent window for the dialog
+
+    Returns:
+        "yes" if user chose to enable autostart
+        "no" if user chose to disable autostart
+        "later" if user wants to be asked later
+        None if dialog was closed without making a choice
+    """
+    dialog = FirstRunDialog(parent)
+    dialog.run()
+    return dialog.result
diff --git a/src/vocalinux/ui/settings_dialog.py b/src/vocalinux/ui/settings_dialog.py
index 89019e0..853034e 100644
--- a/src/vocalinux/ui/settings_dialog.py
+++ b/src/vocalinux/ui/settings_dialog.py
@@ -722,6 +722,7 @@ class SettingsDialog(Gtk.Dialog):
         self.get_content_area().pack_start(scrolled, True, True, 0)
 
         # Build UI sections
+        self._build_general_section()
         self._build_audio_section()
         self._build_engine_section()
         self._build_recognition_section()
@@ -807,6 +808,63 @@ class SettingsDialog(Gtk.Dialog):
         self._populate_audio_devices()
         self.audio_device_combo.connect("changed", self._on_audio_device_changed)
 
+    def _build_general_section(self):
+        """Build the General section with autostart and UI settings."""
+        group = PreferencesGroup(title="General")
+
+        self.autostart_switch = Gtk.Switch()
+        self.autostart_switch.set_tooltip_text("Start Vocalinux automatically when you log in")
+        autostart_row = PreferenceRow(
+            title="Start on Login",
+            subtitle="Automatically start Vocalinux when you log in",
+            widget=self.autostart_switch,
+        )
+        group.add_row(autostart_row)
+
+        self.start_minimized_switch = Gtk.Switch()
+        self.start_minimized_switch.set_tooltip_text("Start minimized to system tray")
+        start_minimized_row = PreferenceRow(
+            title="Start Minimized",
+            subtitle="Start minimized to system tray instead of showing window",
+            widget=self.start_minimized_switch,
+        )
+        group.add_row(start_minimized_row)
+
+        self.content_box.pack_start(group, False, False, 0)
+
+        self.autostart_switch.connect("state-set", self._on_autostart_toggled)
+        self.start_minimized_switch.connect("state-set", self._on_start_minimized_toggled)
+
+    def _on_autostart_toggled(self, widget, state):
+        """Handle toggle of the autostart switch."""
+        if self._initializing or self._applying_settings:
+            return False
+
+        enabled = bool(state)
+        logger.info(f"Autostart toggled: {enabled}")
+
+        from . import autostart_manager
+
+        if autostart_manager.set_autostart(enabled):
+            self.config_manager.set("general", "autostart", enabled)
+            self.config_manager.save_settings()
+            logger.info(f"Autostart {'enabled' if enabled else 'disabled'}")
+            return False
+
+        return True
+
+    def _on_start_minimized_toggled(self, widget, state):
+        """Handle toggle of the start minimized switch."""
+        if self._initializing or self._applying_settings:
+            return False
+
+        enabled = bool(state)
+        logger.info(f"Start minimized toggled: {enabled}")
+        self.config_manager.set("ui", "start_minimized", enabled)
+        self.config_manager.save_settings()
+        logger.info(f"Start minimized {'enabled' if enabled else 'disabled'}")
+        return False
+
     def _build_engine_section(self):
         """Build the Speech Engine section."""
         group = PreferencesGroup(title="Speech Engine")
@@ -879,7 +937,11 @@ class SettingsDialog(Gtk.Dialog):
         legend_box.set_margin_top(4)
         legend_box.set_margin_bottom(4)
 
-        for symbol, text in [("✓", "Downloaded"), ("↓", "Will download"), ("★", "Recommended")]:
+        for symbol, text in [
+            ("✓", "Downloaded"),
+            ("↓", "Will download"),
+            ("★", "Recommended"),
+        ]:
             item = Gtk.Label(label=f"{symbol} {text}")
             item.get_style_context().add_class("status-info")
             legend_box.pack_start(item, False, False, 0)
@@ -1109,6 +1171,15 @@ class SettingsDialog(Gtk.Dialog):
             f"Starting dialog with settings: engine={self.current_engine}, model={self.current_model_size}"
         )
 
+        general_settings = self.config_manager.get_settings().get("general", {})
+        ui_settings = self.config_manager.get_settings().get("ui", {})
+
+        autostart_enabled = general_settings.get("autostart", False)
+        start_minimized = ui_settings.get("start_minimized", False)
+
+        self.autostart_switch.set_active(autostart_enabled)
+        self.start_minimized_switch.set_active(start_minimized)
+
         # Populate engine combo with only available engines
         available_engines = get_available_engines()
         available_count = 0
@@ -1513,10 +1584,16 @@ class SettingsDialog(Gtk.Dialog):
                     except Exception as e:
                         error_msg = str(e)
                         if "cancelled" in error_msg.lower():
-                            GLib.idle_add(download_dialog.set_complete, False, "Download cancelled")
+                            GLib.idle_add(
+                                download_dialog.set_complete,
+                                False,
+                                "Download cancelled",
+                            )
                         elif engine == "whisper" and "no module named" in error_msg.lower():
                             GLib.idle_add(
-                                download_dialog.set_complete, False, "Whisper not installed"
+                                download_dialog.set_complete,
+                                False,
+                                "Whisper not installed",
                             )
                             GLib.idle_add(self._show_whisper_install_dialog)
                         else:
diff --git a/src/vocalinux/ui/tray_indicator.py b/src/vocalinux/ui/tray_indicator.py
index 4b28f88..ab38793 100644
--- a/src/vocalinux/ui/tray_indicator.py
+++ b/src/vocalinux/ui/tray_indicator.py
@@ -28,7 +28,11 @@ except (ImportError, ValueError):
 from gi.repository import GdkPixbuf, GLib, GObject, Gtk
 
 # Import local modules - Use protocols to avoid circular imports
-from ..common_types import RecognitionState, SpeechRecognitionManagerProtocol, TextInjectorProtocol
+from ..common_types import (
+    RecognitionState,
+    SpeechRecognitionManagerProtocol,
+    TextInjectorProtocol,
+)
 
 # Import necessary components
 from .config_manager import ConfigManager  # noqa: E402
@@ -77,6 +81,7 @@ class TrayIndicator:
         self.speech_engine = speech_engine
         self.text_injector = text_injector
         self.config_manager = ConfigManager()  # Added: Initialize ConfigManager
+        self._syncing_autostart_menu = False
 
         # Get configured shortcut from config
         shortcut = self.config_manager.get("shortcuts", "toggle_recognition", "ctrl+ctrl")
@@ -168,6 +173,13 @@ class TrayIndicator:
         # Add menu items
         self._add_menu_item("Start Voice Typing", self._on_start_clicked)
         self._add_menu_item("Stop Voice Typing", self._on_stop_clicked)
+        self._add_menu_separator()
+
+        self._autostart_menu_item = self._add_menu_checkbox(
+            "Start on Login", self._on_autostart_toggled
+        )
+        self._update_autostart_checkbox()
+
         self._add_menu_separator()
         self._add_menu_item("Settings", self._on_settings_clicked)
         self._add_menu_item("View Logs", self._on_logs_clicked)
@@ -211,6 +223,56 @@ class TrayIndicator:
         separator = Gtk.SeparatorMenuItem()
         self.menu.append(separator)
 
+    def _add_menu_checkbox(self, label: str, callback: Callable) -> Gtk.CheckMenuItem:
+        """
+        Add a checkbox menu item to the indicator menu.
+
+        Args:
+            label: The label for the menu item
+            callback: The callback function to call when the item is toggled
+
+        Returns:
+            The checkbox menu item
+        """
+        item = Gtk.CheckMenuItem.new_with_label(label)
+        item.connect("toggled", callback)
+        self.menu.append(item)
+        return item
+
+    def _update_autostart_checkbox(self):
+        """Update the autostart checkbox state based on current config."""
+        from . import autostart_manager
+
+        autostart_enabled = autostart_manager.is_autostart_enabled()
+        config_enabled = self.config_manager.get("general", "autostart", False)
+        if config_enabled != autostart_enabled:
+            self.config_manager.set("general", "autostart", autostart_enabled)
+            self.config_manager.save_settings()
+
+        self._syncing_autostart_menu = True
+        self._autostart_menu_item.set_active(autostart_enabled)
+        self._syncing_autostart_menu = False
+
+    def _on_autostart_toggled(self, widget):
+        """Handle toggle of the Start on Login menu item."""
+        if self._syncing_autostart_menu:
+            return
+
+        enabled = widget.get_active()
+        logger.info(f"Autostart toggled: {enabled}")
+
+        from . import autostart_manager
+
+        if autostart_manager.set_autostart(enabled):
+            self.config_manager.set("general", "autostart", enabled)
+            self.config_manager.save_settings()
+            status = "enabled" if enabled else "disabled"
+            logger.info(f"Autostart {status}")
+        else:
+            self._syncing_autostart_menu = True
+            widget.set_active(not enabled)
+            self._syncing_autostart_menu = False
+
     def _on_recognition_state_changed(self, state: RecognitionState):
         """
         Handle changes in the speech recognition state.
diff --git a/tests/test_autostart_manager.py b/tests/test_autostart_manager.py
new file mode 100644
index 0000000..2f89f30
--- /dev/null
+++ b/tests/test_autostart_manager.py
@@ -0,0 +1,46 @@
+import tempfile
+import unittest
+from pathlib import Path
+from unittest.mock import patch
+
+from vocalinux.ui import autostart_manager
+
+
+class TestAutostartManager(unittest.TestCase):
+    def test_get_autostart_dir_uses_xdg_config_home(self):
+        with patch.dict("os.environ", {"XDG_CONFIG_HOME": "/tmp/vlx-config"}, clear=False):
+            autostart_dir = autostart_manager.get_autostart_dir()
+        self.assertEqual(autostart_dir, Path("/tmp/vlx-config") / "autostart")
+
+    def test_get_exec_command_prefers_installed_command(self):
+        with patch(
+            "vocalinux.ui.autostart_manager.shutil.which",
+            return_value="/usr/bin/vocalinux",
+        ):
+            command = autostart_manager.get_exec_command()
+        self.assertEqual(command, "/usr/bin/vocalinux --start-minimized")
+
+    def test_get_exec_command_falls_back_to_python_module(self):
+        with patch("vocalinux.ui.autostart_manager.shutil.which", return_value=None), patch(
+            "vocalinux.ui.autostart_manager.sys.executable", "/usr/bin/python3"
+        ), patch("vocalinux.ui.autostart_manager.sys.frozen", new=False, create=True):
+            command = autostart_manager.get_exec_command()
+        self.assertEqual(command, "/usr/bin/python3 -m vocalinux.main --start-minimized")
+
+    def test_enable_disable_autostart_creates_and_removes_entry(self):
+        with tempfile.TemporaryDirectory() as tmp_dir:
+            with patch.dict("os.environ", {"XDG_CONFIG_HOME": tmp_dir}, clear=False), patch(
+                "vocalinux.ui.autostart_manager.shutil.which",
+                return_value="/usr/bin/vocalinux",
+            ):
+                enabled = autostart_manager.enable_autostart()
+                self.assertTrue(enabled)
+
+                desktop_file = Path(tmp_dir) / "autostart" / "vocalinux.desktop"
+                self.assertTrue(desktop_file.exists())
+                content = desktop_file.read_text(encoding="utf-8")
+                self.assertIn("Exec=/usr/bin/vocalinux --start-minimized", content)
+
+                disabled = autostart_manager.disable_autostart()
+                self.assertTrue(disabled)
+                self.assertFalse(desktop_file.exists())
diff --git a/tests/test_main.py b/tests/test_main.py
index 4b0b779..583c4ce 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -28,6 +28,7 @@ class TestMainModule(unittest.TestCase):
             self.assertIsNone(args.engine)
             self.assertIsNone(args.language)
             self.assertFalse(args.wayland)
+            self.assertFalse(args.start_minimized)
 
     def test_parse_arguments_custom(self):
         """Test argument parsing with custom values."""
@@ -44,6 +45,7 @@ class TestMainModule(unittest.TestCase):
                 "--language",
                 "fr",
                 "--wayland",
+                "--start-minimized",
             ],
         ):
             args = parse_arguments()
@@ -52,6 +54,7 @@ class TestMainModule(unittest.TestCase):
             self.assertEqual(args.engine, "whisper")
             self.assertEqual(args.language, "fr")
             self.assertTrue(args.wayland)
+            self.assertTrue(args.start_minimized)
 
     def test_parse_arguments_model_choices(self):
         """Test that model only accepts valid choices."""
@@ -139,7 +142,9 @@ class TestMainModule(unittest.TestCase):
 
         # Mock config
         mock_config_instance = MagicMock()
-        mock_config_instance.get_settings.return_value = {}
+        mock_config_instance.get_settings.return_value = {
+            "general": {"first_run": False},
+        }
         mock_config.return_value = mock_config_instance
 
         # Make SpeechRecognitionManager raise an exception
@@ -176,7 +181,10 @@ class TestMainModule(unittest.TestCase):
 
         # Mock ConfigManager to return empty settings (use command-line defaults)
         mock_config_instance = MagicMock()
-        mock_config_instance.get_settings.return_value = {"speech_recognition": {}}
+        mock_config_instance.get_settings.return_value = {
+            "speech_recognition": {},
+            "general": {"first_run": False},
+        }
         mock_config_manager.return_value = mock_config_instance
 
         # Mock objects
@@ -254,7 +262,10 @@ class TestMainModule(unittest.TestCase):
 
         # Mock ConfigManager
         mock_config_instance = MagicMock()
-        mock_config_instance.get_settings.return_value = {"speech_recognition": {}}
+        mock_config_instance.get_settings.return_value = {
+            "speech_recognition": {},
+            "general": {"first_run": False},
+        }
         mock_config_manager.return_value = mock_config_instance
 
         # Mock objects
@@ -288,6 +299,116 @@ class TestMainModule(unittest.TestCase):
             # Verify root logger had setLevel called with DEBUG
             root_logger.setLevel.assert_called()
 
+    @patch("vocalinux.main.check_dependencies")
+    @patch("vocalinux.ui.action_handler.ActionHandler")
+    @patch("vocalinux.speech_recognition.recognition_manager.SpeechRecognitionManager")
+    @patch("vocalinux.text_injection.text_injector.TextInjector")
+    @patch("vocalinux.ui.tray_indicator.TrayIndicator")
+    @patch("vocalinux.ui.first_run_dialog.show_first_run_dialog")
+    @patch("vocalinux.ui.config_manager.ConfigManager")
+    @patch("vocalinux.ui.logging_manager.initialize_logging")
+    def test_main_first_run_later_keeps_prompt_enabled(
+        self,
+        mock_init_logging,
+        mock_config_manager,
+        mock_first_run_dialog,
+        mock_tray,
+        mock_text,
+        mock_speech,
+        mock_action_handler,
+        mock_check_deps,
+    ):
+        """Selecting later on first-run does not disable future prompt."""
+        mock_check_deps.return_value = True
+        mock_first_run_dialog.return_value = "later"
+
+        mock_config_instance = MagicMock()
+        mock_config_instance.get_settings.return_value = {
+            "speech_recognition": {},
+            "general": {"first_run": True},
+        }
+        mock_config_manager.return_value = mock_config_instance
+
+        mock_speech.return_value = MagicMock()
+        mock_text.return_value = MagicMock()
+        mock_tray.return_value = MagicMock()
+        mock_action_instance = MagicMock()
+        mock_action_handler.return_value = mock_action_instance
+
+        with patch("vocalinux.main.parse_arguments") as mock_parse:
+            mock_args = MagicMock()
+            mock_args.debug = False
+            mock_args.model = "small"
+            mock_args.engine = "vosk"
+            mock_args.language = "en-us"
+            mock_args.wayland = False
+            mock_parse.return_value = mock_args
+
+            with patch("vocalinux.main.logger"):
+                main()
+
+        self.assertFalse(
+            any(
+                call.args == ("general", "first_run", False)
+                for call in mock_config_instance.set.call_args_list
+            )
+        )
+        mock_config_instance.save_settings.assert_not_called()
+
+    @patch("vocalinux.main.check_dependencies")
+    @patch("vocalinux.ui.action_handler.ActionHandler")
+    @patch("vocalinux.speech_recognition.recognition_manager.SpeechRecognitionManager")
+    @patch("vocalinux.text_injection.text_injector.TextInjector")
+    @patch("vocalinux.ui.tray_indicator.TrayIndicator")
+    @patch("vocalinux.ui.first_run_dialog.show_first_run_dialog")
+    @patch("vocalinux.ui.config_manager.ConfigManager")
+    @patch("vocalinux.ui.logging_manager.initialize_logging")
+    def test_main_start_minimized_skips_first_run_prompt(
+        self,
+        mock_init_logging,
+        mock_config_manager,
+        mock_first_run_dialog,
+        mock_tray,
+        mock_text,
+        mock_speech,
+        mock_action_handler,
+        mock_check_deps,
+    ):
+        mock_check_deps.return_value = True
+
+        mock_config_instance = MagicMock()
+        mock_config_instance.get_settings.return_value = {
+            "speech_recognition": {},
+            "general": {"first_run": True},
+        }
+        mock_config_manager.return_value = mock_config_instance
+
+        mock_speech.return_value = MagicMock()
+        mock_text.return_value = MagicMock()
+        mock_tray.return_value = MagicMock()
+        mock_action_handler.return_value = MagicMock()
+
+        with patch("vocalinux.main.parse_arguments") as mock_parse:
+            mock_args = MagicMock()
+            mock_args.debug = False
+            mock_args.model = "small"
+            mock_args.engine = "vosk"
+            mock_args.language = "en-us"
+            mock_args.wayland = False
+            mock_args.start_minimized = True
+            mock_parse.return_value = mock_args
+
+            with patch("vocalinux.main.logger"):
+                main()
+
+        mock_first_run_dialog.assert_not_called()
+        self.assertFalse(
+            any(
+                call.args[0:2] == ("general", "first_run")
+                for call in mock_config_instance.set.call_args_list
+            )
+        )
+
 
 class TestCheckDependencies(unittest.TestCase):
     """Test cases for check_dependencies function."""
@@ -429,7 +550,8 @@ class TestMainConfigPrecedence(unittest.TestCase):
                 "engine": "vosk",
                 "model_size": "small",
                 "language": "en-us",
-            }
+            },
+            "general": {"first_run": False},
         }
         mock_config_manager.return_value = mock_config_instance
 
@@ -445,7 +567,16 @@ class TestMainConfigPrecedence(unittest.TestCase):
 
         # Simulate CLI args being set
         with patch(
-            "sys.argv", ["vocalinux", "--engine", "whisper", "--model", "large", "--language", "fr"]
+            "sys.argv",
+            [
+                "vocalinux",
+                "--engine",
+                "whisper",
+                "--model",
+                "large",
+                "--language",
+                "fr",
+            ],
         ):
             with patch("vocalinux.main.logger"):
                 main()
@@ -488,6 +619,7 @@ class TestMainConfigPrecedence(unittest.TestCase):
             "audio": {
                 "device_index": 2,
             },
+            "general": {"first_run": False},
         }
         mock_config_manager.return_value = mock_config_instance
 
diff --git a/uninstall.sh b/uninstall.sh
index 38366bc..459a53a 100755
--- a/uninstall.sh
+++ b/uninstall.sh
@@ -27,6 +27,30 @@ command_exists() {
     command -v "$1" >/dev/null 2>&1
 }
 
+get_vocalinux_pids() {
+    pgrep -f "vocalinux" 2>/dev/null | while read -r pid; do
+        [ -z "$pid" ] && continue
+
+        if [ "$pid" = "$$" ] || [ "$pid" = "$PPID" ]; then
+            continue
+        fi
+
+        local stat
+        stat=$(ps -o stat= -p "$pid" 2>/dev/null | awk '{print $1}')
+        if [[ "$stat" == Z* ]]; then
+            continue
+        fi
+
+        local cmd
+        cmd=$(ps -o args= -p "$pid" 2>/dev/null)
+        if [[ "$cmd" == *"install.sh"* ]] || [[ "$cmd" == *"uninstall.sh"* ]]; then
+            continue
+        fi
+
+        echo "$pid"
+    done
+}
+
 # Function to safely remove a file or directory
 safe_remove() {
     local path="$1"
@@ -51,7 +75,8 @@ safe_remove() {
 kill_vocalinux_processes() {
     print_info "Checking for running Vocalinux processes..."
     
-    local PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+    local PIDS
+    PIDS=$(get_vocalinux_pids || true)
     
     if [ -n "$PIDS" ]; then
         print_warning "Found running Vocalinux process(es): $PIDS"
@@ -69,7 +94,8 @@ kill_vocalinux_processes() {
         echo "$PIDS" | xargs -r kill -TERM 2>/dev/null || true
         sleep 2
         
-        local REMAINING_PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+        local REMAINING_PIDS
+        REMAINING_PIDS=$(get_vocalinux_pids || true)
         
         if [ -n "$REMAINING_PIDS" ]; then
             print_warning "Some processes still running, forcing termination..."
@@ -77,7 +103,8 @@ kill_vocalinux_processes() {
             sleep 1
         fi
         
-        local FINAL_PIDS=$(pgrep -f "vocalinux" 2>/dev/null || true)
+        local FINAL_PIDS
+        FINAL_PIDS=$(get_vocalinux_pids || true)
         if [ -n "$FINAL_PIDS" ]; then
             print_error "Warning: Could not terminate all Vocalinux processes: $FINAL_PIDS"
             print_error "You may need to manually kill these processes before continuing."
@@ -145,6 +172,7 @@ done
 CONFIG_DIR="${XDG_CONFIG_HOME:-$HOME/.config}/vocalinux"
 DATA_DIR="${XDG_DATA_HOME:-$HOME/.local/share}/vocalinux"
 DESKTOP_DIR="${XDG_DATA_HOME:-$HOME/.local/share}/applications"
+AUTOSTART_DIR="${XDG_CONFIG_HOME:-$HOME/.config}/autostart"
 ICON_DIR="${XDG_DATA_HOME:-$HOME/.local/share}/icons/hicolor/scalable/apps"
 
 # Directories created by curl-based installation
@@ -233,6 +261,8 @@ remove_application_files() {
     
     # Remove desktop entry
     safe_remove "$DESKTOP_DIR/vocalinux.desktop" "desktop entry"
+
+    safe_remove "$AUTOSTART_DIR/vocalinux.desktop" "autostart desktop entry"
     
     # Remove icons
     print_info "Removing application icons..."
@@ -337,6 +367,11 @@ verify_uninstallation() {
         print_warning "Desktop entry still exists: $DESKTOP_DIR/vocalinux.desktop"
         ((ISSUES++))
     fi
+
+    if [ -f "$AUTOSTART_DIR/vocalinux.desktop" ]; then
+        print_warning "Autostart desktop entry still exists: $AUTOSTART_DIR/vocalinux.desktop"
+        ((ISSUES++))
+    fi
     
     # Check if any icons still exist
     local ICON_COUNT=0