diff --git a/.vscode/settings.json b/.vscode/settings.json
index 92184457..9211c3a5 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -98,6 +98,7 @@
     "tmpfilename",
     "ungroup",
     "unnegated",
+    "Unraid",
     "upgrader",
     "urandom",
     "urlsafe",
diff --git a/app/__init__.py b/app/__init__.py
index e69de29b..96b3d490 100644
--- a/app/__init__.py
+++ b/app/__init__.py
@@ -0,0 +1,13 @@
+import os
+import sys
+from pathlib import Path
+
+if base_dir := os.environ.get("YTP_CONFIG_PATH"):
+    base_dir = Path(base_dir)
+    user_site = base_dir / f"python{sys.version_info.major}.{sys.version_info.minor}-packages"
+
+    if not user_site.exists():
+        user_site.mkdir(parents=True, exist_ok=True)
+
+    if user_site.is_dir() and str(user_site) not in sys.path:
+        sys.path.insert(0, str(user_site))
diff --git a/app/library/PackageInstaller.py b/app/library/PackageInstaller.py
index ef6faa97..65cceba2 100644
--- a/app/library/PackageInstaller.py
+++ b/app/library/PackageInstaller.py
@@ -1,13 +1,20 @@
 import importlib
+import importlib.metadata
 import logging
 import os
 import subprocess
 import sys
 from pathlib import Path
 
+import httpx
+
 LOG = logging.getLogger("package_installer")
 
 
+def parse_version(v: str) -> tuple[int, ...]:
+    return tuple(int("".join(filter(str.isdigit, part)) or "0") for part in v.strip().split("."))
+
+
 class Packages:
     def __init__(self, env: str | None, file: str | None, upgrade: bool = False):
         from_env = env.split() if env else []
@@ -30,30 +37,68 @@ class Packages:
 
 
 class PackageInstaller:
-    """
-    This class is responsible for installing and upgrading pip packages.
-    """
+    user_site: Path | None = None
+
+    def __init__(self):
+        if base_dir := os.environ.get("YTP_CONFIG_PATH"):
+            base_dir = Path(base_dir)
+            self.user_site = base_dir / f"python{sys.version_info.major}.{sys.version_info.minor}-packages"
+            self.user_site.mkdir(parents=True, exist_ok=True)
+
+            if str(self.user_site) not in sys.path:
+                sys.path.insert(0, str(self.user_site))
 
     def action(self, pkg: str, upgrade: bool = False):
-        try:
-            importlib.import_module(pkg)
-            if upgrade is False:
-                LOG.info(f"'{pkg}' is already installed. Skipping upgrades. as requested.")
+        current_version = self._get_installed_version(pkg)
+
+        if upgrade and current_version:
+            latest_version = self._get_latest_version(pkg)
+            if latest_version and parse_version(current_version) >= parse_version(latest_version):
+                LOG.info(f"'{pkg}' is already the latest version ({current_version}). Skipping upgrade.")
                 return
 
-            LOG.info(f"'{pkg}' is already installed. Checking for upgrades...")
-            subprocess.run(
-                [sys.executable, "-m", "pip", "install", "--upgrade", pkg],
-                check=True,
-                creationflags=subprocess.CREATE_NO_WINDOW if os.name == "nt" else 0,
-            )
-        except ImportError:
+        if current_version:
+            LOG.info(f"'{pkg}' is already installed (version: {current_version}). Proceeding with upgrade...")
+        else:
             LOG.info(f"'{pkg}' is not installed. Installing...")
-            subprocess.run(
-                [sys.executable, "-m", "pip", "install", pkg],
-                check=True,
-                creationflags=subprocess.CREATE_NO_WINDOW if os.name == "nt" else 0,
-            )
+
+        self._install_pkg(pkg)
+
+    def _get_installed_version(self, pkg: str) -> str | None:
+        try:
+            return importlib.metadata.version(pkg)
+        except importlib.metadata.PackageNotFoundError:
+            return None
+
+    def _get_latest_version(self, pkg: str) -> str | None:
+        url = f"https://pypi.org/pypi/{pkg}/json"
+        try:
+            with httpx.Client(timeout=5.0) as client:
+                resp = client.get(url)
+                if 200 == resp.status_code:
+                    return resp.json()["info"]["version"]
+                LOG.warning(f"Failed to fetch '{pkg}' info: HTTP {resp.status_code}")
+        except Exception as e:
+            LOG.warning(f"Error while querying PyPI for '{pkg}': {e}")
+        return None
+
+    def _install_pkg(self, pkg: str):
+        subprocess.run(
+            [
+                sys.executable,
+                "-m",
+                "pip",
+                "install",
+                "--upgrade",
+                "--disable-pip-version-check",
+                "--target",
+                str(self.user_site),
+                "--no-warn-script-location",
+                pkg,
+            ],
+            check=True,
+            creationflags=subprocess.CREATE_NO_WINDOW if os.name == "nt" else 0,
+        )
 
     def check(self, pkgs: Packages):
         """
@@ -63,7 +108,7 @@ class PackageInstaller:
             pkgs (GetPackages): the class with packages and their settings.
 
         """
-        if not pkgs.has_packages():
+        if not pkgs.has_packages() or not self.user_site:
             return
 
         LOG.info(f"Checking for user pip packages: {', '.join(pkgs.packages)}")
diff --git a/app/routes/api/dev.py b/app/routes/api/dev.py
index c53fe397..778cbe26 100644
--- a/app/routes/api/dev.py
+++ b/app/routes/api/dev.py
@@ -40,3 +40,29 @@ async def debug_asyncio(config: Config, encoder: Encoder) -> Response:
         dumps=encoder.encode,
     )
 
+
+@route("GET", "api/dev/pip", "check_pip_packages")
+async def check_pip_packages(config: Config, encoder: Encoder) -> Response:
+    pkgs = config.pip_packages.split(" ") if config.pip_packages else []
+    if not pkgs:
+        return web.json_response(
+            data={"message": "No pip packages configured."},
+            status=web.HTTPOk.status_code,
+        )
+
+    def _get_installed_version(pkg: str) -> str | None:
+        try:
+            import importlib.metadata
+
+            return importlib.metadata.version(pkg)
+        except importlib.metadata.PackageNotFoundError:
+            return None
+
+    response = {}
+    for pkg in pkgs:
+        if not (pkg := pkg.strip()):
+            continue
+
+        response.update({pkg: _get_installed_version(pkg)})
+
+    return web.json_response(data=response, status=web.HTTPOk.status_code, dumps=encoder.encode)