diff --git a/build-dist-windows.sh b/build-dist-windows.sh
index a05d4de..b585b6a 100644
--- a/build-dist-windows.sh
+++ b/build-dist-windows.sh
@@ -43,7 +43,6 @@ CORE_DEPS=(
     "pyyaml>=6.0"
     "mutagen>=1.47.0"
     "pillow>=10.0.0"
-    "packaging>=23.0"
 )
 
 # Windows-specific dependencies
diff --git a/media_server/main.py b/media_server/main.py
index 55f7190..d6fd69b 100644
--- a/media_server/main.py
+++ b/media_server/main.py
@@ -2,6 +2,7 @@
 
 import argparse
 import logging
+import socket
 import sys
 from contextlib import asynccontextmanager
 from pathlib import Path
@@ -259,6 +260,19 @@ def main():
             print("\nAuthentication is DISABLED (no tokens configured)")
         return
 
+    # Check if port is available before starting
+    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as sock:
+        try:
+            sock.bind((args.host if args.host != "0.0.0.0" else "127.0.0.1", args.port))
+        except OSError:
+            print(
+                f"ERROR: Port {args.port} is already in use. "
+                f"Another instance of Media Server may be running.\n"
+                f"Stop the other process or use --port to pick a different port.",
+                file=sys.stderr,
+            )
+            sys.exit(1)
+
     from .tray import PYSTRAY_AVAILABLE, TrayManager
 
     use_tray = PYSTRAY_AVAILABLE and not args.no_tray
diff --git a/media_server/services/update_checker.py b/media_server/services/update_checker.py
index a242cf6..37b451c 100644
--- a/media_server/services/update_checker.py
+++ b/media_server/services/update_checker.py
@@ -3,10 +3,9 @@
 import asyncio
 import logging
 import re
+from functools import total_ordering
 from typing import Any, Optional
 
-from packaging.version import Version
-
 from .release_provider import ReleaseProvider
 from .websocket_manager import ws_manager
 
@@ -15,23 +14,67 @@ logger = logging.getLogger(__name__)
 _PRE_PATTERN = re.compile(
     r"^(\d+\.\d+\.\d+)[-.]?(alpha|beta|rc)[.-]?(\d+)$", re.IGNORECASE
 )
-_PRE_MAP = {"alpha": "a", "beta": "b", "rc": "rc"}
+_PRE_ORDER = {"alpha": 0, "beta": 1, "rc": 2}
 
 
-def _parse_version(raw: str) -> Version:
-    """Normalize a version tag to PEP 440 for correct comparison.
+@total_ordering
+class _Version:
+    """Lightweight PEP 440-ish version for comparison without packaging dep.
+
+    Supports: X.Y.Z and X.Y.Z-{alpha,beta,rc}.N
+    Pre-releases sort before the corresponding stable release.
+    """
+
+    __slots__ = ("_release", "_pre")
+
+    def __init__(self, release: tuple[int, ...], pre: Optional[tuple[int, int]]) -> None:
+        self._release = release
+        self._pre = pre
+
+    def __eq__(self, other: object) -> bool:
+        if not isinstance(other, _Version):
+            return NotImplemented
+        return self._release == other._release and self._pre == other._pre
+
+    def __lt__(self, other: object) -> bool:
+        if not isinstance(other, _Version):
+            return NotImplemented
+        if self._release != other._release:
+            return self._release < other._release
+        # No pre-release (stable) is greater than any pre-release
+        if self._pre is None and other._pre is None:
+            return False
+        if self._pre is not None and other._pre is None:
+            return True
+        if self._pre is None and other._pre is not None:
+            return False
+        return self._pre < other._pre  # type: ignore[operator]
+
+    def __repr__(self) -> str:
+        v = ".".join(str(p) for p in self._release)
+        if self._pre is not None:
+            labels = {0: "alpha", 1: "beta", 2: "rc"}
+            v += f"-{labels[self._pre[0]]}.{self._pre[1]}"
+        return f"_Version('{v}')"
+
+
+def _parse_version(raw: str) -> _Version:
+    """Parse a version tag for comparison.
 
     Examples:
-        v0.3.0-alpha.1 → 0.3.0a1  (pre-release, sorts below 0.3.0)
-        v0.3.0-rc.3    → 0.3.0rc3
-        v1.0.0         → 1.0.0
+        v0.3.0-alpha.1 → (0,3,0) pre=(0,1)  (sorts below 0.3.0)
+        v0.3.0-rc.3    → (0,3,0) pre=(2,3)
+        v1.0.0         → (1,0,0) pre=None
     """
     cleaned = raw.lstrip("v").strip()
     m = _PRE_PATTERN.match(cleaned)
     if m:
-        base, pre_label, pre_num = m.group(1), m.group(2).lower(), m.group(3)
-        cleaned = f"{base}{_PRE_MAP[pre_label]}{pre_num}"
-    return Version(cleaned)
+        base = tuple(int(x) for x in m.group(1).split("."))
+        pre_label = m.group(2).lower()
+        pre_num = int(m.group(3))
+        return _Version(base, (_PRE_ORDER[pre_label], pre_num))
+    release = tuple(int(x) for x in cleaned.split("."))
+    return _Version(release, None)
 
 
 class UpdateChecker:
diff --git a/pyproject.toml b/pyproject.toml
index 43dd227..cbfb136 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -32,7 +32,6 @@ dependencies = [
     "pyyaml>=6.0",
     "mutagen>=1.47.0",
     "pillow>=10.0.0",
-    "packaging>=23.0",
 ]
 
 [project.optional-dependencies]