diff --git a/Borealis.ps1 b/Borealis.ps1
index f1bb5f3..068955e 100644
--- a/Borealis.ps1
+++ b/Borealis.ps1
@@ -958,6 +958,7 @@ switch ($choice) {
                 New-Item -Path $dataDestination -ItemType Directory -Force | Out-Null
                 Copy-Item "$dataSource\Server\Python_API_Endpoints" $dataDestination -Recurse
                 Copy-Item "$dataSource\Server\Sounds"               $dataDestination -Recurse
+                Copy-Item "$dataSource\Server\Modules"               $dataDestination -Recurse
                 Copy-Item "$dataSource\Server\server.py"            $dataDestination
                 Copy-Item "$dataSource\Server\job_scheduler.py"     $dataDestination 
             }
diff --git a/Data/Server/Modules/crypto/certificates.py b/Data/Server/Modules/crypto/certificates.py
index adbae73..b50c40f 100644
--- a/Data/Server/Modules/crypto/certificates.py
+++ b/Data/Server/Modules/crypto/certificates.py
@@ -42,7 +42,11 @@ def ensure_certificate(common_name: str = "Borealis Server") -> Tuple[Path, Path
         try:
             with _CERT_FILE.open("rb") as fh:
                 cert = x509.load_pem_x509_certificate(fh.read())
-            if cert.not_valid_after.replace(tzinfo=timezone.utc) <= datetime.now(tz=timezone.utc):
+            try:
+                expiry = cert.not_valid_after_utc  # type: ignore[attr-defined]
+            except AttributeError:
+                expiry = cert.not_valid_after.replace(tzinfo=timezone.utc)
+            if expiry <= datetime.now(tz=timezone.utc):
                 regenerate = True
         except Exception:
             regenerate = True
@@ -130,4 +134,3 @@ def build_ssl_context() -> ssl.SSLContext:
 def certificate_paths() -> Tuple[str, str, str]:
     cert_path, key_path, bundle_path = ensure_certificate()
     return str(cert_path), str(key_path), str(bundle_path)
-
diff --git a/Data/Server/WebUI/vite.config.mts b/Data/Server/WebUI/vite.config.mts
index f3d5aaa..c43aa0a 100644
--- a/Data/Server/WebUI/vite.config.mts
+++ b/Data/Server/WebUI/vite.config.mts
@@ -4,13 +4,32 @@ import react from '@vitejs/plugin-react';
 import path from 'path';
 import fs from 'fs';
 
-const defaultCert = path.resolve(__dirname, '../certs/borealis-server-cert.pem');
-const defaultKey = path.resolve(__dirname, '../certs/borealis-server-key.pem');
+const certCandidates = [
+  process.env.BOREALIS_TLS_CERT,
+  path.resolve(__dirname, '../certs/borealis-server-cert.pem'),
+  path.resolve(__dirname, '../../Data/Server/certs/borealis-server-cert.pem'),
+] as const;
 
-const certPath = process.env.BOREALIS_TLS_CERT ?? defaultCert;
-const keyPath = process.env.BOREALIS_TLS_KEY ?? defaultKey;
+const keyCandidates = [
+  process.env.BOREALIS_TLS_KEY,
+  path.resolve(__dirname, '../certs/borealis-server-key.pem'),
+  path.resolve(__dirname, '../../Data/Server/certs/borealis-server-key.pem'),
+] as const;
 
-const httpsOptions = fs.existsSync(certPath) && fs.existsSync(keyPath)
+const pickFirst = (candidates: readonly (string | undefined)[]) => {
+  for (const candidate of candidates) {
+    if (!candidate) continue;
+    if (fs.existsSync(candidate)) {
+      return candidate;
+    }
+  }
+  return undefined;
+};
+
+const certPath = pickFirst(certCandidates);
+const keyPath = pickFirst(keyCandidates);
+
+const httpsOptions = certPath && keyPath
   ? {
       cert: fs.readFileSync(certPath),
       key: fs.readFileSync(keyPath),
diff --git a/Data/Server/server.py b/Data/Server/server.py
index d943ef3..f657bef 100644
--- a/Data/Server/server.py
+++ b/Data/Server/server.py
@@ -18,6 +18,22 @@ Section Guide:
   * WebSocket Event Handling and Entrypoint
 """
 
+import os
+import sys
+
+# Ensure the modular server package is importable when the runtime is launched
+# from a packaged directory (e.g., Server/Borealis). We look for the canonical
+# Data/Server location as well as a sibling Modules folder.
+_SERVER_DIR = os.path.abspath(os.path.dirname(__file__))
+_SEARCH_ROOTS = [
+    _SERVER_DIR,
+    os.path.abspath(os.path.join(_SERVER_DIR, "..", "..", "Data", "Server")),
+]
+for root in _SEARCH_ROOTS:
+    modules_dir = os.path.join(root, "Modules")
+    if os.path.isdir(modules_dir) and root not in sys.path:
+        sys.path.insert(0, root)
+
 import eventlet
 # Monkey-patch stdlib for cooperative sockets (keep real threads for tpool usage)
 eventlet.monkey_patch(thread=False)
@@ -34,7 +50,6 @@ from werkzeug.middleware.proxy_fix import ProxyFix
 from itsdangerous import URLSafeTimedSerializer, BadSignature, SignatureExpired
 
 import time
-import os  # To Read Production ReactJS Server Folder
 import json  # For reading workflow JSON files
 import shutil  # For moving workflow files and folders
 from typing import List, Dict, Tuple, Optional, Any, Set, Sequence
@@ -8125,5 +8140,11 @@ def relay_ansible_run(data):
 
 if __name__ == "__main__":
     # Use SocketIO runner so WebSocket transport works with eventlet.
-    ssl_context = certificates.build_ssl_context()
-    socketio.run(app, host="0.0.0.0", port=5000, ssl_context=ssl_context)
+    # Eventlet's WSGI server expects raw cert/key paths rather than an ssl.SSLContext.
+    socketio.run(
+        app,
+        host="0.0.0.0",
+        port=5000,
+        certfile=TLS_CERT_PATH,
+        keyfile=TLS_KEY_PATH,
+    )