diff --git a/scripts/windows-debug/check-tee-command.ps1 b/scripts/windows-debug/check-tee-command.ps1
new file mode 100644
index 000000000..46fa7f093
--- /dev/null
+++ b/scripts/windows-debug/check-tee-command.ps1
@@ -0,0 +1,142 @@
+#!/usr/bin/env pwsh
+# Script to check if tee command is available on Windows
+# Usage: .\check-tee-command.ps1
+
+Write-Host "Checking for 'tee' command availability on Windows..." -ForegroundColor Cyan
+Write-Host ""
+
+# Store original PATH
+$originalPath = $env:PATH
+
+# Method 1: Using where.exe
+Write-Host "Method 1: Using where.exe" -ForegroundColor Yellow
+try {
+    $whereResult = where.exe tee 2>&1
+    if ($LASTEXITCODE -eq 0) {
+        Write-Host "  Found tee at: $whereResult" -ForegroundColor Green
+    } else {
+        Write-Host "  tee not found via where.exe" -ForegroundColor Red
+    }
+} catch {
+    Write-Host "  Error checking with where.exe: $_" -ForegroundColor Red
+}
+
+Write-Host ""
+
+# Method 2: Using Get-Command
+Write-Host "Method 2: Using Get-Command" -ForegroundColor Yellow
+try {
+    $getCommandResult = Get-Command tee -ErrorAction Stop
+    Write-Host "  Found tee:" -ForegroundColor Green
+    Write-Host "    Name: $($getCommandResult.Name)"
+    Write-Host "    CommandType: $($getCommandResult.CommandType)"
+    Write-Host "    Source: $($getCommandResult.Source)"
+    Write-Host "    Version: $($getCommandResult.Version)"
+} catch {
+    Write-Host "  tee not found via Get-Command" -ForegroundColor Red
+}
+
+Write-Host ""
+
+# Method 3: Check common locations
+Write-Host "Method 3: Checking common locations" -ForegroundColor Yellow
+$commonPaths = @(
+    "C:\Program Files\Git\usr\bin\tee.exe",
+    "C:\Program Files (x86)\Git\usr\bin\tee.exe",
+    "C:\tools\msys64\usr\bin\tee.exe",
+    "C:\msys64\usr\bin\tee.exe",
+    "C:\cygwin64\bin\tee.exe",
+    "C:\cygwin\bin\tee.exe"
+)
+
+$found = $false
+foreach ($path in $commonPaths) {
+    if (Test-Path $path) {
+        Write-Host "  Found at: $path" -ForegroundColor Green
+        $found = $true
+    }
+}
+
+if (-not $found) {
+    Write-Host "  tee not found in common locations" -ForegroundColor Red
+}
+
+Write-Host ""
+
+# Method 4: Check if it's a PowerShell alias
+Write-Host "Method 4: Checking PowerShell aliases" -ForegroundColor Yellow
+$alias = Get-Alias tee -ErrorAction SilentlyContinue
+if ($alias) {
+    Write-Host "  Found PowerShell alias:" -ForegroundColor Green
+    Write-Host "    Name: $($alias.Name)"
+    Write-Host "    Definition: $($alias.Definition)"
+} else {
+    Write-Host "  No PowerShell alias for tee" -ForegroundColor Yellow
+}
+
+Write-Host ""
+
+# Method 5: Python check (what the test uses)
+Write-Host "Method 5: Python shutil.which() check" -ForegroundColor Yellow
+$pythonCheck = python -c "import shutil; print(shutil.which('tee'))"
+if ($pythonCheck -and $pythonCheck -ne "None") {
+    Write-Host "  Python found tee at: $pythonCheck" -ForegroundColor Green
+} else {
+    Write-Host "  Python shutil.which() did not find tee" -ForegroundColor Red
+}
+
+Write-Host ""
+
+# Method 6: Try adding Git for Windows to PATH if it exists
+Write-Host "Method 6: Adding Git for Windows to PATH temporarily" -ForegroundColor Yellow
+$gitPaths = @(
+    "C:\Program Files\Git\usr\bin",
+    "C:\Program Files (x86)\Git\usr\bin"
+)
+
+$addedToPath = $false
+foreach ($gitPath in $gitPaths) {
+    if (Test-Path $gitPath) {
+        Write-Host "  Found Git directory: $gitPath" -ForegroundColor Green
+        $env:PATH = "$gitPath;$env:PATH"
+        $teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+        if ($teeCheck -and $teeCheck -ne "None") {
+            Write-Host "  tee is now available at: $teeCheck" -ForegroundColor Green
+            $addedToPath = $true
+            break
+        }
+    }
+}
+
+if (-not $addedToPath) {
+    # Restore original PATH if we didn't find tee
+    $env:PATH = $originalPath
+    Write-Host "  Could not add Git for Windows tee to PATH" -ForegroundColor Red
+}
+
+Write-Host ""
+Write-Host "========== SUMMARY ==========" -ForegroundColor Cyan
+if ($whereResult -or $getCommandResult -or $found -or ($pythonCheck -and $pythonCheck -ne "None") -or $addedToPath) {
+    Write-Host "tee command is available" -ForegroundColor Green
+    Write-Host ""
+    Write-Host "The test_stdio_context_manager_exiting test should run." -ForegroundColor Green
+    if ($addedToPath) {
+        Write-Host ""
+        Write-Host "Note: Git for Windows tee was added to PATH for this session." -ForegroundColor Yellow
+        Write-Host "To make this permanent, add this to your PowerShell profile:" -ForegroundColor Yellow
+        Write-Host "  `$env:PATH = `"C:\Program Files\Git\usr\bin;`$env:PATH`"" -ForegroundColor Cyan
+    }
+} else {
+    Write-Host "tee command is NOT available" -ForegroundColor Red
+    Write-Host ""
+    Write-Host "The test_stdio_context_manager_exiting test will be SKIPPED." -ForegroundColor Yellow
+    Write-Host ""
+    Write-Host "To install tee on Windows, you can:" -ForegroundColor Cyan
+    Write-Host "  1. Install Git for Windows (includes tee in Git Bash)"
+    Write-Host "  2. Install WSL (Windows Subsystem for Linux)"
+    Write-Host "  3. Install MSYS2 or Cygwin"
+    Write-Host "  4. Use PowerShell's Tee-Object cmdlet (different syntax)"
+}
+
+# Restore original PATH
+$env:PATH = $originalPath
\ No newline at end of file
diff --git a/scripts/windows-debug/diagnose-environment.ps1 b/scripts/windows-debug/diagnose-environment.ps1
new file mode 100644
index 000000000..5d49480b2
--- /dev/null
+++ b/scripts/windows-debug/diagnose-environment.ps1
@@ -0,0 +1,152 @@
+#!/usr/bin/env pwsh
+# Script to diagnose environment differences that might cause CI flakiness
+# Usage: .\diagnose-environment.ps1
+
+Write-Host "Diagnosing Windows environment for stdio test issues..." -ForegroundColor Cyan
+Write-Host ""
+
+# System Information
+Write-Host "=== SYSTEM INFORMATION ===" -ForegroundColor Yellow
+Write-Host "Windows Version:"
+(Get-CimInstance Win32_OperatingSystem).Version
+Write-Host "Windows Build:"
+(Get-ItemProperty "HKLM:\SOFTWARE\Microsoft\Windows NT\CurrentVersion").DisplayVersion
+Write-Host ""
+
+# Python Information
+Write-Host "=== PYTHON INFORMATION ===" -ForegroundColor Yellow
+Write-Host "Python Version:"
+python --version
+Write-Host ""
+Write-Host "Python Build Info:"
+python -c "import sys; print(f'Version: {sys.version}')"
+python -c "import sys; print(f'Platform: {sys.platform}')"
+python -c "import sys; print(f'Windows Version: {sys.getwindowsversion()}')"
+Write-Host ""
+
+# Check subprocess configuration
+Write-Host "=== SUBPROCESS CONFIGURATION ===" -ForegroundColor Yellow
+python -c @"
+import subprocess
+import sys
+print(f'CREATE_NO_WINDOW available: {hasattr(subprocess, "CREATE_NO_WINDOW")}')
+print(f'CREATE_NEW_PROCESS_GROUP available: {hasattr(subprocess, "CREATE_NEW_PROCESS_GROUP")}')
+print(f'Windows subprocess startup info: {hasattr(subprocess, "STARTUPINFO")}')
+
+# Check handle inheritance defaults
+import os
+print(f'\nHandle inheritance (os.O_NOINHERIT): {hasattr(os, "O_NOINHERIT")}')
+
+# Check asyncio event loop
+import asyncio
+try:
+    loop = asyncio.get_event_loop_policy()
+    print(f'Event loop policy: {type(loop).__name__}')
+except:
+    print('Event loop policy: Unable to determine')
+"@
+Write-Host ""
+
+# Check for Job Objects support
+Write-Host "=== JOB OBJECTS SUPPORT ===" -ForegroundColor Yellow
+python -c @"
+try:
+    import win32job
+    import win32api
+    print('pywin32 available: Yes')
+    print(f'win32job version: {win32job.__file__}')
+    
+    # Try to create a job object
+    try:
+        job = win32job.CreateJobObject(None, '')
+        win32api.CloseHandle(job)
+        print('Job Object creation: Success')
+    except Exception as e:
+        print(f'Job Object creation: Failed - {e}')
+except ImportError:
+    print('pywin32 available: No (Job Objects not available)')
+"@
+Write-Host ""
+
+# Check process limits
+Write-Host "=== PROCESS LIMITS ===" -ForegroundColor Yellow
+python -c @"
+import os
+import psutil
+proc = psutil.Process(os.getpid())
+print(f'Open handles: {proc.num_handles()}')
+print(f'Open files: {len(proc.open_files())}')
+
+# Check system-wide limits
+print(f'Total processes: {len(psutil.pids())}')
+"@
+Write-Host ""
+
+# Check security software
+Write-Host "=== SECURITY SOFTWARE ===" -ForegroundColor Yellow
+Get-CimInstance -Namespace "root\SecurityCenter2" -ClassName AntiVirusProduct -ErrorAction SilentlyContinue | 
+    Select-Object displayName, productState | Format-Table
+Write-Host ""
+
+# Test rapid process creation
+Write-Host "=== RAPID PROCESS CREATION TEST ===" -ForegroundColor Yellow
+Write-Host "Testing rapid tee process creation/destruction..."
+$testScript = @'
+import time
+import subprocess
+import sys
+
+failures = 0
+times = []
+
+for i in range(20):
+    start = time.time()
+    try:
+        # Create process with same flags as stdio client
+        proc = subprocess.Popen(
+            ['tee'],
+            stdin=subprocess.PIPE,
+            stdout=subprocess.PIPE,
+            stderr=subprocess.PIPE,
+            creationflags=getattr(subprocess, 'CREATE_NO_WINDOW', 0)
+        )
+        proc.stdin.close()
+        proc.wait(timeout=0.5)
+        elapsed = time.time() - start
+        times.append(elapsed)
+    except Exception as e:
+        failures += 1
+        print(f"  Iteration {i+1}: FAILED - {e}")
+    
+    if (i+1) % 5 == 0:
+        avg_time = sum(times) / len(times) if times else 0
+        print(f"  Completed {i+1}/20 (avg: {avg_time*1000:.1f}ms)")
+
+print(f"\nFailures: {failures}/20")
+if times:
+    print(f"Average time: {sum(times)/len(times)*1000:.1f}ms")
+    print(f"Max time: {max(times)*1000:.1f}ms")
+'@
+
+python -c $testScript
+Write-Host ""
+
+# Environment variables that might affect subprocess
+Write-Host "=== RELEVANT ENVIRONMENT VARIABLES ===" -ForegroundColor Yellow
+@("COMSPEC", "PATH", "PYTHONPATH", "PYTHONASYNCIODEBUG") | ForEach-Object {
+    $value = [Environment]::GetEnvironmentVariable($_)
+    if ($value) {
+        Write-Host "$_`:"
+        Write-Host "  $value" -ForegroundColor Gray
+    }
+}
+Write-Host ""
+
+Write-Host "=== DIAGNOSIS COMPLETE ===" -ForegroundColor Cyan
+Write-Host ""
+Write-Host "Share this output when reporting the flakiness issue." -ForegroundColor Yellow
+Write-Host "Key differences to look for between local and CI:" -ForegroundColor Yellow
+Write-Host "  - Windows version/build" -ForegroundColor Gray
+Write-Host "  - Python build details" -ForegroundColor Gray
+Write-Host "  - Security software presence" -ForegroundColor Gray
+Write-Host "  - Process creation timing" -ForegroundColor Gray
\ No newline at end of file
diff --git a/scripts/windows-debug/setup-environment.ps1 b/scripts/windows-debug/setup-environment.ps1
new file mode 100644
index 000000000..25dd44e27
--- /dev/null
+++ b/scripts/windows-debug/setup-environment.ps1
@@ -0,0 +1,59 @@
+#!/usr/bin/env pwsh
+# Script to set up the environment for running stdio tests on Windows
+# This adds Git for Windows tools to PATH if available
+# Usage: . .\setup-environment.ps1 (note the dot-sourcing)
+
+Write-Host "Setting up environment for stdio tests..." -ForegroundColor Cyan
+Write-Host ""
+
+# Check if Git for Windows is installed
+$gitPaths = @(
+    "C:\Program Files\Git\usr\bin",
+    "C:\Program Files (x86)\Git\usr\bin"
+)
+
+$gitFound = $false
+$gitPath = ""
+
+foreach ($path in $gitPaths) {
+    if (Test-Path $path) {
+        $gitPath = $path
+        $gitFound = $true
+        break
+    }
+}
+
+if ($gitFound) {
+    Write-Host "Found Git for Windows at: $gitPath" -ForegroundColor Green
+    
+    # Add to PATH
+    $env:PATH = "$gitPath;$env:PATH"
+    
+    # Verify tee is available
+    $teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+    if ($teeCheck -and $teeCheck -ne "None") {
+        Write-Host "Successfully added tee to PATH: $teeCheck" -ForegroundColor Green
+        Write-Host ""
+        Write-Host "Environment is ready for stdio tests!" -ForegroundColor Green
+        Write-Host ""
+        Write-Host "You can now run the test scripts or individual tests:" -ForegroundColor Cyan
+        Write-Host "  .\test-stdio-flakiness-200-runs.ps1"
+        Write-Host "  .\test-stdio-flakiness-until-failure.ps1"
+        Write-Host "  .\test-stdio-verbose-debug.ps1"
+        Write-Host ""
+        Write-Host "Or run individual tests with:" -ForegroundColor Cyan
+        Write-Host "  uv run pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -v -o addopts="""""
+    } else {
+        Write-Host "WARNING: Git path was added but tee is still not available" -ForegroundColor Yellow
+    }
+} else {
+    Write-Host "Git for Windows not found in standard locations." -ForegroundColor Red
+    Write-Host ""
+    Write-Host "Please install Git for Windows from: https://gitforwindows.org/" -ForegroundColor Yellow
+    Write-Host "Or manually add the Git usr\bin directory to your PATH." -ForegroundColor Yellow
+}
+
+Write-Host ""
+Write-Host "Note: This only affects the current PowerShell session." -ForegroundColor Gray
+Write-Host "To make changes permanent, add to your PowerShell profile:" -ForegroundColor Gray
+Write-Host '  $env:PATH = "C:\Program Files\Git\usr\bin;$env:PATH"' -ForegroundColor Cyan
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-flakiness-200-runs.ps1 b/scripts/windows-debug/test-stdio-flakiness-200-runs.ps1
new file mode 100644
index 000000000..26bdddd6b
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-flakiness-200-runs.ps1
@@ -0,0 +1,55 @@
+#!/usr/bin/env pwsh
+# Script to run test_stdio_context_manager_exiting 200 times to detect flakiness
+# Usage: .\test-stdio-flakiness-200-runs.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Running test_stdio_context_manager_exiting 200 times to detect flakiness..." -ForegroundColor Cyan
+Write-Host "Test: tests/client/test_stdio.py::test_stdio_context_manager_exiting" -ForegroundColor Yellow
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+$startTime = Get-Date
+$count = 0
+$failures = 0
+$failedRuns = @()
+
+for ($i = 1; $i -le 200; $i++) {
+    Write-Host "Run $i of 200..." -NoNewline
+    
+    $output = uv run --frozen pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -xvs -o addopts="" 2>&1
+    $exitCode = $LASTEXITCODE
+    
+    if ($exitCode -ne 0) {
+        $failures++
+        $failedRuns += $i
+        Write-Host " FAILED" -ForegroundColor Red
+        Write-Host "Failure output:" -ForegroundColor Red
+        Write-Host $output
+        Write-Host ""
+    } else {
+        Write-Host " PASSED" -ForegroundColor Green
+    }
+}
+
+$endTime = Get-Date
+$duration = $endTime - $startTime
+
+Write-Host ""
+Write-Host "========== SUMMARY ==========" -ForegroundColor Cyan
+Write-Host "Total runs: 200"
+Write-Host "Successful runs: $(200 - $failures)" -ForegroundColor Green
+Write-Host "Failed runs: $failures" -ForegroundColor Red
+if ($failures -gt 0) {
+    Write-Host "Failed on runs: $($failedRuns -join ', ')" -ForegroundColor Red
+}
+Write-Host "Duration: $($duration.ToString())"
+Write-Host "Failure rate: $([math]::Round(($failures / 200) * 100, 2))%"
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-flakiness-until-failure.ps1 b/scripts/windows-debug/test-stdio-flakiness-until-failure.ps1
new file mode 100644
index 000000000..1a9df0e40
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-flakiness-until-failure.ps1
@@ -0,0 +1,53 @@
+#!/usr/bin/env pwsh
+# Script to run test_stdio_context_manager_exiting until it fails
+# Usage: .\test-stdio-flakiness-until-failure.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Running test_stdio_context_manager_exiting until failure..." -ForegroundColor Cyan
+Write-Host "Test: tests/client/test_stdio.py::test_stdio_context_manager_exiting" -ForegroundColor Yellow
+Write-Host "Press Ctrl+C to stop" -ForegroundColor Gray
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+$startTime = Get-Date
+$i = 0
+
+while ($true) {
+    $i++
+    Write-Host "Run $i..." -NoNewline
+    
+    $output = uv run --frozen pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -xvs -o addopts="" 2>&1
+    $exitCode = $LASTEXITCODE
+    
+    if ($exitCode -ne 0) {
+        $endTime = Get-Date
+        $duration = $endTime - $startTime
+        
+        Write-Host " FAILED!" -ForegroundColor Red
+        Write-Host ""
+        Write-Host "========== FAILURE DETECTED ==========" -ForegroundColor Red
+        Write-Host "Failed on run: $i" -ForegroundColor Red
+        Write-Host "Time until failure: $($duration.ToString())" -ForegroundColor Yellow
+        Write-Host ""
+        Write-Host "Failure output:" -ForegroundColor Red
+        Write-Host $output
+        break
+    } else {
+        Write-Host " PASSED" -ForegroundColor Green
+    }
+    
+    # Small delay to prevent overwhelming the system
+    Start-Sleep -Milliseconds 100
+}
+
+Write-Host ""
+Write-Host "Exiting after failure detection." -ForegroundColor Cyan
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-parallel-flakiness.ps1 b/scripts/windows-debug/test-stdio-parallel-flakiness.ps1
new file mode 100644
index 000000000..af3280175
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-parallel-flakiness.ps1
@@ -0,0 +1,94 @@
+#!/usr/bin/env pwsh
+# Script to test for flakiness when running tests in parallel (like CI does)
+# This simulates the xdist environment where the issue occurs
+# Usage: .\test-stdio-parallel-flakiness.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Testing stdio with parallel execution to simulate CI environment..." -ForegroundColor Cyan
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+Write-Host "Running tests with different parallel configurations..." -ForegroundColor Yellow
+Write-Host ""
+
+# Test 1: Run with 4 workers (default CI behavior)
+Write-Host "Test 1: Running with 4 parallel workers (CI default)..." -ForegroundColor Cyan
+$failures1 = 0
+for ($i = 1; $i -le 20; $i++) {
+    Write-Host "  Run $i..." -NoNewline
+    $output = uv run --frozen pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -v -n 4 2>&1
+    if ($LASTEXITCODE -ne 0) {
+        $failures1++
+        Write-Host " FAILED" -ForegroundColor Red
+    } else {
+        Write-Host " PASSED" -ForegroundColor Green
+    }
+}
+Write-Host "  Result: $failures1 failures out of 20 runs" -ForegroundColor $(if ($failures1 -eq 0) { "Green" } else { "Red" })
+Write-Host ""
+
+# Test 2: Run with 2 workers
+Write-Host "Test 2: Running with 2 parallel workers..." -ForegroundColor Cyan
+$failures2 = 0
+for ($i = 1; $i -le 20; $i++) {
+    Write-Host "  Run $i..." -NoNewline
+    $output = uv run --frozen pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -v -n 2 2>&1
+    if ($LASTEXITCODE -ne 0) {
+        $failures2++
+        Write-Host " FAILED" -ForegroundColor Red
+    } else {
+        Write-Host " PASSED" -ForegroundColor Green
+    }
+}
+Write-Host "  Result: $failures2 failures out of 20 runs" -ForegroundColor $(if ($failures2 -eq 0) { "Green" } else { "Red" })
+Write-Host ""
+
+# Test 3: Run all stdio tests in parallel (simulates real CI)
+Write-Host "Test 3: Running ALL stdio tests with 4 workers (full CI simulation)..." -ForegroundColor Cyan
+$failures3 = 0
+for ($i = 1; $i -le 10; $i++) {
+    Write-Host "  Run $i..." -NoNewline
+    $output = uv run --frozen pytest tests/client/test_stdio.py -v -n 4 2>&1
+    if ($LASTEXITCODE -ne 0) {
+        $failures3++
+        Write-Host " FAILED" -ForegroundColor Red
+        # Show which test failed
+        $failedTest = $output | Select-String "FAILED tests/client/test_stdio.py::" | Select-Object -First 1
+        if ($failedTest) {
+            Write-Host "    Failed: $failedTest" -ForegroundColor Red
+        }
+    } else {
+        Write-Host " PASSED" -ForegroundColor Green
+    }
+}
+Write-Host "  Result: $failures3 failures out of 10 runs" -ForegroundColor $(if ($failures3 -eq 0) { "Green" } else { "Red" })
+Write-Host ""
+
+# Summary
+Write-Host "========== SUMMARY ==========" -ForegroundColor Cyan
+Write-Host "4 workers (single test): $failures1/20 failures"
+Write-Host "2 workers (single test): $failures2/20 failures"
+Write-Host "4 workers (all tests):   $failures3/10 failures"
+Write-Host ""
+
+if ($failures1 -gt 0 -or $failures2 -gt 0 -or $failures3 -gt 0) {
+    Write-Host "FLAKINESS DETECTED with parallel execution!" -ForegroundColor Red
+    Write-Host ""
+    Write-Host "This confirms the issue is related to parallel test execution." -ForegroundColor Yellow
+    Write-Host "The race condition likely involves:" -ForegroundColor Yellow
+    Write-Host "  - Windows Job Object handle management" -ForegroundColor Gray
+    Write-Host "  - Process cleanup timing with multiple workers" -ForegroundColor Gray
+    Write-Host "  - Handle inheritance between test processes" -ForegroundColor Gray
+} else {
+    Write-Host "No flakiness detected in this run." -ForegroundColor Green
+    Write-Host "The issue might require specific timing conditions to reproduce." -ForegroundColor Yellow
+}
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-simple.ps1 b/scripts/windows-debug/test-stdio-simple.ps1
new file mode 100644
index 000000000..3cf877ca0
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-simple.ps1
@@ -0,0 +1,40 @@
+#!/usr/bin/env pwsh
+# Simple script to run the test without xdist
+# Usage: .\test-stdio-simple.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Running test_stdio_context_manager_exiting with xdist disabled..." -ForegroundColor Cyan
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+Write-Host "tee found at: $teeCheck" -ForegroundColor Green
+Write-Host ""
+
+# Run the test with the working method
+Write-Host "Running test with -o addopts='' to override xdist..." -ForegroundColor Yellow
+uv run --frozen pytest tests/client/test_stdio.py::test_stdio_context_manager_exiting -xvs -o addopts=""
+$exitCode = $LASTEXITCODE
+
+Write-Host ""
+if ($exitCode -eq 0) {
+    Write-Host "Test PASSED!" -ForegroundColor Green
+    Write-Host ""
+    Write-Host "You can now use the other scripts to test for flakiness:" -ForegroundColor Cyan
+    Write-Host "  .\test-stdio-flakiness-200-runs.ps1" 
+    Write-Host "  .\test-stdio-flakiness-until-failure.ps1"
+    Write-Host "  .\test-stdio-verbose-debug.ps1"
+} else {
+    Write-Host "Test FAILED with exit code $exitCode" -ForegroundColor Red
+    Write-Host ""
+    Write-Host "Try running with verbose debug:" -ForegroundColor Yellow
+    Write-Host "  .\test-stdio-verbose-debug.ps1"
+}
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-stress-race.ps1 b/scripts/windows-debug/test-stdio-stress-race.ps1
new file mode 100644
index 000000000..633fa7b20
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-stress-race.ps1
@@ -0,0 +1,125 @@
+#!/usr/bin/env pwsh
+# Script to stress test the specific race condition in stdio cleanup
+# This creates many processes rapidly to expose handle/job object races
+# Usage: .\test-stdio-stress-race.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Stress testing stdio cleanup race conditions..." -ForegroundColor Cyan
+Write-Host "This test creates many processes rapidly to expose timing issues." -ForegroundColor Yellow
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+# Create a Python script that runs the test many times in quick succession
+$stressScript = @'
+import asyncio
+import sys
+import time
+from pathlib import Path
+
+# Add parent directories to path
+sys.path.insert(0, str(Path(__file__).parent.parent.parent))
+
+from mcp.client.stdio import stdio_client, StdioServerParameters
+
+async def rapid_test(test_id: int):
+    """Run a single test iteration"""
+    try:
+        async with stdio_client(StdioServerParameters(command="tee")) as (_, _):
+            pass
+        return True, None
+    except Exception as e:
+        return False, str(e)
+
+async def stress_test(iterations: int, concurrent: int):
+    """Run many tests concurrently"""
+    print(f"Running {iterations} tests with {concurrent} concurrent...")
+    
+    failures = 0
+    errors = []
+    start_time = time.time()
+    
+    # Run in batches
+    for batch in range(0, iterations, concurrent):
+        batch_size = min(concurrent, iterations - batch)
+        tasks = [rapid_test(batch + i) for i in range(batch_size)]
+        results = await asyncio.gather(*tasks)
+        
+        for success, error in results:
+            if not success:
+                failures += 1
+                if error and error not in errors:
+                    errors.append(error)
+        
+        # Progress indicator
+        if (batch + batch_size) % 100 == 0:
+            print(f"  Completed {batch + batch_size}/{iterations} tests...")
+    
+    duration = time.time() - start_time
+    return failures, errors, duration
+
+async def main():
+    # Test different concurrency levels
+    configs = [
+        (100, 1),    # Sequential
+        (100, 2),    # Low concurrency
+        (100, 5),    # Medium concurrency
+        (100, 10),   # High concurrency
+    ]
+    
+    for iterations, concurrent in configs:
+        print(f"\nTest: {iterations} iterations, {concurrent} concurrent")
+        failures, errors, duration = await stress_test(iterations, concurrent)
+        
+        print(f"  Duration: {duration:.2f}s")
+        print(f"  Failures: {failures}/{iterations}")
+        if errors:
+            print(f"  Unique errors: {len(errors)}")
+            for error in errors[:3]:  # Show first 3 errors
+                print(f"    - {error}")
+        
+        if failures > 0:
+            print("  RACE CONDITION DETECTED!" if concurrent > 1 else "  FAILURE DETECTED!")
+
+if __name__ == "__main__":
+    asyncio.run(main())
+'@
+
+# Save the stress test script
+$scriptPath = Join-Path $PSScriptRoot "stress_test.py"
+$stressScript | Out-File -FilePath $scriptPath -Encoding UTF8
+
+Write-Host "Running stress tests..." -ForegroundColor Cyan
+Write-Host ""
+
+# Run the stress test
+uv run python $scriptPath
+
+$exitCode = $LASTEXITCODE
+
+# Clean up
+Remove-Item $scriptPath -ErrorAction SilentlyContinue
+
+Write-Host ""
+Write-Host "========== ANALYSIS ==========" -ForegroundColor Cyan
+
+if ($exitCode -ne 0) {
+    Write-Host "Stress test failed to complete." -ForegroundColor Red
+} else {
+    Write-Host "Stress test completed." -ForegroundColor Green
+    Write-Host ""
+    Write-Host "If failures increased with concurrency, it indicates:" -ForegroundColor Yellow
+    Write-Host "  - Race condition in process cleanup" -ForegroundColor Gray
+    Write-Host "  - Job Object handle conflicts" -ForegroundColor Gray
+    Write-Host "  - Windows handle inheritance issues" -ForegroundColor Gray
+    Write-Host ""
+    Write-Host "This matches the CI flakiness pattern where parallel tests fail." -ForegroundColor Yellow
+}
\ No newline at end of file
diff --git a/scripts/windows-debug/test-stdio-verbose-debug.ps1 b/scripts/windows-debug/test-stdio-verbose-debug.ps1
new file mode 100644
index 000000000..593c216cf
--- /dev/null
+++ b/scripts/windows-debug/test-stdio-verbose-debug.ps1
@@ -0,0 +1,52 @@
+#!/usr/bin/env pwsh
+# Script to run test_stdio_context_manager_exiting with maximum debugging output
+# Usage: .\test-stdio-verbose-debug.ps1
+#
+# Prerequisites: Run . .\setup-environment.ps1 first to ensure tee is available
+
+Write-Host "Running test_stdio_context_manager_exiting with verbose debug output..." -ForegroundColor Cyan
+Write-Host ""
+
+# Check if tee is available
+$teeCheck = python -c "import shutil; print(shutil.which('tee'))"
+if (-not $teeCheck -or $teeCheck -eq "None") {
+    Write-Host "ERROR: tee command not found!" -ForegroundColor Red
+    Write-Host "Please run: . .\setup-environment.ps1" -ForegroundColor Yellow
+    Write-Host "(Note the dot at the beginning to source the script)" -ForegroundColor Yellow
+    exit 1
+}
+
+# Set environment variables for debugging
+$env:PYTHONFAULTHANDLER = "1"
+$env:PYTEST_CURRENT_TEST = "1"
+
+Write-Host "Environment variables set:" -ForegroundColor Yellow
+Write-Host "  PYTHONFAULTHANDLER = 1 (enables Python fault handler)"
+Write-Host ""
+
+Write-Host "Running test with maximum verbosity..." -ForegroundColor Cyan
+Write-Host ""
+
+# Run the test with all debugging options
+uv run --frozen pytest `
+    tests/client/test_stdio.py::test_stdio_context_manager_exiting `
+    -xvs `
+    -o addopts="" `
+    --log-cli-level=DEBUG `
+    --log-cli-format="%(asctime)s [%(levelname)s] %(name)s: %(message)s" `
+    --capture=no `
+    --tb=long `
+    --full-trace
+
+$exitCode = $LASTEXITCODE
+
+Write-Host ""
+if ($exitCode -eq 0) {
+    Write-Host "Test PASSED" -ForegroundColor Green
+} else {
+    Write-Host "Test FAILED with exit code: $exitCode" -ForegroundColor Red
+}
+
+# Clean up environment variables
+Remove-Item Env:PYTHONFAULTHANDLER -ErrorAction SilentlyContinue
+Remove-Item Env:PYTEST_CURRENT_TEST -ErrorAction SilentlyContinue
\ No newline at end of file
diff --git a/scripts/windows-debug/test.txt b/scripts/windows-debug/test.txt
new file mode 100644
index 000000000..e69de29bb
diff --git a/test.txt b/test.txt
new file mode 100644
index 000000000..5ca294497
--- /dev/null
+++ b/test.txt
@@ -0,0 +1,6 @@
+hello
+test
+test
+test
+test
+test