diff --git a/scripts/bootstrap.ps1 b/scripts/bootstrap.ps1
index 12d6452..e502024 100644
--- a/scripts/bootstrap.ps1
+++ b/scripts/bootstrap.ps1
@@ -32,6 +32,10 @@ param(
     [switch]$Quiet
 )
 
+# Track whether the user chose an interactive auto-fix (so we can auto-remove .pth files)
+$AutoFixInteractive = $false
+)
+
 function Write-Log {
     param([string]$msg,[string]$lvl="INFO")
     if (-not $Quiet) {
@@ -294,6 +298,7 @@ print(json.dumps(out))"
                 }
                 $ans = Read-Host "Attempt automatic fix now? (y/N)"
                 if ($ans -eq 'y' -or $ans -eq 'Y') {
+                    $AutoFixInteractive = $true
                     try { & $venvPython -m pip uninstall urllib3-future -y } catch {}
                     try { & $venvPython -m pip install --upgrade --force-reinstall urllib3 } catch { Write-Log "pip install failed: $_" "ERROR"; exit 7 }
                     try { & $venvPython -m pip install niquests -U } catch { Write-Log "pip install niquests failed: $_" "ERROR" }
@@ -308,8 +313,8 @@ print(json.dumps(out))"
                             exit 7
                         }
                         Write-Log ("Found interfering .pth files:`n" + ($pths -join "`n")) "ERROR"
-                        if ($RemovePth) {
-                            Write-Log "Removing .pth files as requested..." "INFO"
+                        if ($RemovePth -or $AutoFixInteractive -or $FixUrllib3) {
+                            Write-Log "Removing .pth files automatically..." "INFO"
                             if (RemovePthAndVerify -python $venvPython -paths $pths) {
                                 Write-Log "Success: urllib3 problems resolved after .pth removal; continuing." "INFO"
                             } else {