diff --git a/scripts/config.py b/scripts/config.py
index 4486b55..0a6bee5 100755
--- a/scripts/config.py
+++ b/scripts/config.py
@@ -36,7 +36,7 @@
     '--no-default-browser-check'
 ]
 
-USER_AGENT = 'Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36'
+USER_AGENT = 'Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/131.0.0.0 Safari/537.36'
 
 # Timeouts
 LOGIN_TIMEOUT_MINUTES = 10
diff --git a/scripts/run.py b/scripts/run.py
index 7c47a92..0b2ab77 100755
--- a/scripts/run.py
+++ b/scripts/run.py
@@ -4,8 +4,15 @@
 Ensures all scripts run with the correct virtual environment
 """
 
-import os
 import sys
+
+# Force UTF-8 for stdout/stderr so emoji prints don't crash on Windows,
+# where the default console encoding is cp1252.
+if hasattr(sys.stdout, 'reconfigure'):
+    sys.stdout.reconfigure(encoding='utf-8', errors='replace')
+    sys.stderr.reconfigure(encoding='utf-8', errors='replace')
+
+import os
 import subprocess
 from pathlib import Path
 
@@ -34,8 +41,11 @@ def ensure_venv():
         print("🔧 First-time setup: Creating virtual environment...")
         print("   This may take a minute...")
 
-        # Run setup with system Python
-        result = subprocess.run([sys.executable, str(setup_script)])
+        # Run setup with system Python; propagate UTF-8 so the setup
+        # script's emoji prints survive on Windows.
+        setup_env = os.environ.copy()
+        setup_env.setdefault('PYTHONIOENCODING', 'utf-8')
+        result = subprocess.run([sys.executable, str(setup_script)], env=setup_env)
         if result.returncode != 0:
             print("❌ Failed to set up environment")
             sys.exit(1)
@@ -86,9 +96,15 @@ def main():
     # Build command
     cmd = [str(venv_python), str(script_path)] + script_args
 
+    # Propagate UTF-8 to the child process so emoji prints in the called
+    # script (auth_manager / notebook_manager / ask_question) don't crash
+    # on Windows.
+    child_env = os.environ.copy()
+    child_env.setdefault('PYTHONIOENCODING', 'utf-8')
+
     # Run the script
     try:
-        result = subprocess.run(cmd)
+        result = subprocess.run(cmd, env=child_env)
         sys.exit(result.returncode)
     except KeyboardInterrupt:
         print("\n⚠️ Interrupted by user")
diff --git a/scripts/setup_environment.py b/scripts/setup_environment.py
index a4167d0..bebd08e 100755
--- a/scripts/setup_environment.py
+++ b/scripts/setup_environment.py
@@ -50,9 +50,11 @@ def ensure_venv(self) -> bool:
         if self.requirements_file.exists():
             print("📦 Installing dependencies...")
             try:
-                # Upgrade pip first
+                # Upgrade pip via `python -m pip` (instead of `pip.exe install
+                # --upgrade pip`) so Windows can replace pip without hitting a
+                # FileLock on the running pip.exe.
                 subprocess.run(
-                    [str(self.venv_pip), "install", "--upgrade", "pip"],
+                    [str(self.venv_python), "-m", "pip", "install", "--upgrade", "pip"],
                     check=True,
                     capture_output=True,
                     text=True