diff --git a/openadapt/app/tray.py b/openadapt/app/tray.py
index 805a39b60..6240a2f97 100644
--- a/openadapt/app/tray.py
+++ b/openadapt/app/tray.py
@@ -3,6 +3,21 @@
 usage: `python -m openadapt.app.tray` or `poetry run app`
 """
 
+import sys
+import asyncio
+import os
+
+# Fix for Windows ProactorEventLoop
+if sys.platform == "win32":
+    try:
+        if isinstance(
+            asyncio.get_event_loop_policy(), asyncio.WindowsProactorEventLoopPolicy
+        ):
+            # Use WindowsSelectorEventLoopPolicy instead
+            asyncio.set_event_loop_policy(asyncio.WindowsSelectorEventLoopPolicy())
+    except Exception as e:
+        print(f"Failed to set event loop policy: {e}")
+
 from datetime import datetime
 from functools import partial
 from pprint import pformat
@@ -10,8 +25,6 @@
 from typing import Any, Callable
 import inspect
 import multiprocessing
-import os
-import sys
 
 from pyqttoast import Toast, ToastButtonAlignment, ToastIcon, ToastPosition, ToastPreset
 from PySide6.QtCore import QMargins, QObject, QSize, Qt, QThread, Signal
@@ -33,7 +46,7 @@
     QWidget,
 )
 
-from openadapt.app import quick_record, stop_record, FPATH
+from openadapt.app import FPATH, quick_record, stop_record
 from openadapt.app.dashboard.run import cleanup as cleanup_dashboard
 from openadapt.app.dashboard.run import run as run_dashboard
 from openadapt.build_utils import is_running_from_executable
@@ -109,8 +122,9 @@ class SystemTrayIcon:
 
     def __init__(self) -> None:
         """Initialize the system tray icon."""
-        self.app = QApplication([])
-
+        self.app = QApplication.instance()
+        if not self.app:
+            self.app = QApplication([])
         if sys.platform == "darwin":
             # hide Dock icon while allowing focus on dialogs
             # (must come after QApplication())
diff --git a/openadapt/entrypoint.py b/openadapt/entrypoint.py
index 1d05a5cdc..de8f64f6f 100644
--- a/openadapt/entrypoint.py
+++ b/openadapt/entrypoint.py
@@ -1,30 +1,138 @@
 """Entrypoint for OpenAdapt."""
 
 import multiprocessing
+import sys
+import requests
 
-if __name__ == "__main__":
-    # This needs to be called before any code that uses multiprocessing
-    multiprocessing.freeze_support()
+from PySide6.QtCore import QObject, QTimer, Signal
+from PySide6.QtWidgets import QApplication
 
 from openadapt.build_utils import redirect_stdout_stderr
-from openadapt.error_reporting import configure_error_reporting
+from openadapt.config import config
 from openadapt.custom_logger import logger
+from openadapt.splash_screen import LoadingScreen
 
 
-def run_openadapt() -> None:
-    """Run OpenAdapt."""
-    with redirect_stdout_stderr():
+class LoadingManager(QObject):
+    """Manages the loading stages and progress updates."""
+
+    progress_updated = Signal(int, str)
+    loading_complete = Signal()
+
+    def __init__(self, splash_screen: LoadingScreen, app: QApplication) -> None:
+        """Initialize the loading manager."""
+        super().__init__()
+        self.splash = splash_screen
+        self.app = app
+        self.progress_updated.connect(self._update_progress)
+        self.loading_complete.connect(self._on_loading_complete)
+        self.dashboard_check_attempts = 0
+        self.is_ready = False
+        self.dashboard_timer = None
+
+    def _update_progress(self, value: int, message: str) -> None:
+        """Update progress bar and process events."""
+        if not self.is_ready:
+            self.splash.update_progress(value)
+            self.splash.update_status(message)
+            self.app.processEvents()
+            logger.debug(f"Progress: {value}% - {message}")
+
+    def _on_loading_complete(self) -> None:
+        """Handle completion of loading sequence."""
+        self.is_ready = True
+        if self.dashboard_timer:
+            self.dashboard_timer.stop()
+        QTimer.singleShot(500, self.splash.hide)
+        QTimer.singleShot(600, self.app.quit)
+
+    def check_dashboard(self) -> None:
+        """Check if dashboard is responsive and handle loading completion."""
         try:
-            from openadapt.alembic.context_loader import load_alembic_context
-            from openadapt.app import tray
+            url = f"http://localhost:{config.DASHBOARD_CLIENT_PORT}"
+            response = requests.get(url, timeout=1)
+            if response.status_code == 200:
+                self.progress_updated.emit(100, "Ready!")
+                self.loading_complete.emit()
+                return
+        except requests.RequestException:
+            pass
+
+    def start_dashboard_monitoring(self) -> None:
+        """Start dashboard monitoring using Qt timer."""
+        self.dashboard_timer = QTimer(self)
+        self.dashboard_timer.timeout.connect(self.check_dashboard)
+        self.dashboard_timer.start(100)  # Check every 100ms
+
+    def start_loading_sequence(self) -> bool:
+        """Execute the loading sequence with visible progress updates."""
+        try:
+            # Initial setup - 0%
+            self.progress_updated.emit(0, "Initializing...")
+
+            # Configuration - 20%
+            self.progress_updated.emit(20, "Loading configuration...")
             from openadapt.config import print_config
 
             print_config()
+
+            # Error reporting setup - 40%
+            self.progress_updated.emit(40, "Configuring error reporting...")
+            from openadapt.error_reporting import configure_error_reporting
+
             configure_error_reporting()
+
+            # Database context - 60%
+            self.progress_updated.emit(60, "Loading database context...")
+            from openadapt.alembic.context_loader import load_alembic_context
+
             load_alembic_context()
-            tray._run()
+
+            # System tray setup - 80%
+            self.progress_updated.emit(80, "Starting system tray...")
+
+            return True
+
+        except Exception as e:
+            logger.error(f"Loading sequence failed: {e}")
+            return False
+
+
+def run_tray() -> None:
+    """Run the openadapt tray."""
+    from openadapt.app import tray
+
+    tray._run()
+
+
+def run_openadapt() -> None:
+    """Run OpenAdapt."""
+    with redirect_stdout_stderr():
+        try:
+            app = QApplication(sys.argv)
+            splash = LoadingScreen()
+            splash.show()
+
+            loading_manager = LoadingManager(splash, app)
+
+            if not loading_manager.start_loading_sequence():
+                raise Exception("Loading sequence failed")
+
+            tray_process = multiprocessing.Process(target=run_tray, daemon=False)
+            tray_process.start()
+
+            if not tray_process.is_alive():
+                raise Exception("Tray process failed to start")
+
+            loading_manager.start_dashboard_monitoring()
+
+            app.exec()
+
         except Exception as exc:
             logger.exception(exc)
+            if "tray_process" in locals() and tray_process and tray_process.is_alive():
+                tray_process.terminate()
+            sys.exit(1)
 
 
 if __name__ == "__main__":
diff --git a/openadapt/splash_screen.py b/openadapt/splash_screen.py
new file mode 100644
index 000000000..add3446b2
--- /dev/null
+++ b/openadapt/splash_screen.py
@@ -0,0 +1,91 @@
+"""Modern minimal splash screen for OpenAdapt with improved responsiveness."""
+
+from PySide6.QtCore import Qt, QTimer
+from PySide6.QtGui import QColor, QPixmap
+from PySide6.QtWidgets import QApplication, QLabel, QProgressBar, QSplashScreen
+
+
+class LoadingScreen(QSplashScreen):
+    """A minimal splash screen for."""
+
+    def __init__(self) -> None:
+        """Initialize the loading screen."""
+        pixmap = QPixmap(400, 100)
+        pixmap.fill(QColor(0, 0, 0, 180))
+
+        super().__init__(pixmap)
+
+        self.title_label = QLabel("OpenAdapt", self)
+        self.title_label.setGeometry(0, 15, 400, 30)
+        self.title_label.setAlignment(Qt.AlignCenter)
+        self.title_label.setStyleSheet(
+            """
+            QLabel {
+                color: #FFFFFF;
+                font-family: Arial;
+                font-size: 20px;
+                font-weight: bold;
+            }
+        """
+        )
+
+        self.progress_bar = QProgressBar(self)
+        self.progress_bar.setGeometry(50, 55, 300, 6)
+        self.progress_bar.setRange(0, 100)
+        self.progress_bar.setValue(0)
+        self.progress_bar.setTextVisible(False)
+
+        self.status_label = QLabel(self)
+        self.status_label.setGeometry(0, 70, 400, 20)
+        self.status_label.setAlignment(Qt.AlignCenter)
+
+        self.setWindowFlags(Qt.WindowStaysOnTopHint | Qt.FramelessWindowHint)
+
+        self.progress_bar.setStyleSheet(
+            """
+            QProgressBar {
+                border: none;
+                background: rgba(255, 255, 255, 0.1);
+                border-radius: 3px;
+            }
+            QProgressBar::chunk {
+                background: qlineargradient(x1:0, y1:0, x2:1, y2:0,
+                    stop:0 #2196F3, stop:1 #64B5F6);
+                border-radius: 3px;
+            }
+        """
+        )
+
+        self.status_label.setStyleSheet(
+            """
+            QLabel {
+                color: #CCCCCC;
+                font-size: 11px;
+                font-family: Arial;
+            }
+        """
+        )
+
+    def update_status(self, message: str) -> None:
+        """Update the status message displayed on the splash screen."""
+        self.status_label.setText(message)
+        self.repaint()
+        QApplication.processEvents()
+
+    def update_progress(self, value: int) -> None:
+        """Update progress value with immediate visual feedback."""
+        value = max(0, min(100, value))
+        # for smooth progress updates
+        QTimer.singleShot(0, lambda: self._do_update(value))
+
+    def _do_update(self, value: int) -> None:
+        """Internal method to perform the actual progress update."""
+        self.progress_bar.setValue(value)
+        self.repaint()
+        QApplication.processEvents()
+
+    def show(self) -> None:
+        """Show the splash screen."""
+        super().show()
+        self.raise_()
+        QApplication.processEvents()