diff --git a/scripts/bootstrap.ps1 b/scripts/bootstrap.ps1
index 83e2f8e..2b2e6ff 100644
--- a/scripts/bootstrap.ps1
+++ b/scripts/bootstrap.ps1
@@ -27,6 +27,7 @@ param(
     [switch]$NoInstall,
     [switch]$NoPlaywright,
     [string]$PlaywrightBrowsers = "chromium",
+    [switch]$FixUrllib3,
     [switch]$Quiet
 )
 
@@ -191,8 +192,41 @@ if (-not $NoInstall) {
             Write-Log "  $ $venvPython -m pip uninstall urllib3-future -y" "INFO"
             Write-Log "  $ $venvPython -m pip install --upgrade --force-reinstall urllib3" "INFO"
             Write-Log "  $ $venvPython -m pip install niquests -U" "INFO"
-            Write-Log "Aborting bootstrap to avoid leaving a broken environment." "ERROR"
-            exit 7
+
+            if ($FixUrllib3) {
+                Write-Log "Attempting automatic fix (--FixUrllib3)..." "INFO"
+                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" }
+                & $venvPython -c "import sys; from SYS.env_check import check_urllib3_compat; ok, msg = check_urllib3_compat(); print(msg); sys.exit(0 if ok else 2)"
+                if ($LASTEXITCODE -ne 0) {
+                    Write-Log "Automatic fix failed; aborting." "ERROR"
+                    exit 7
+                } else {
+                    Write-Log "Success: urllib3 problems appear resolved; continuing." "INFO"
+                }
+            } else {
+                if ($Quiet) {
+                    Write-Log "Bootstrap detected a potentially broken 'urllib3' installation. Use -FixUrllib3 to attempt an automatic fix." "ERROR"
+                    exit 7
+                }
+                $ans = Read-Host "Attempt automatic fix now? (y/N)"
+                if ($ans -eq 'y' -or $ans -eq 'Y') {
+                    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" }
+                    & $venvPython -c "import sys; from SYS.env_check import check_urllib3_compat; ok, msg = check_urllib3_compat(); print(msg); sys.exit(0 if ok else 2)"
+                    if ($LASTEXITCODE -ne 0) {
+                        Write-Log "Automatic fix failed; aborting." "ERROR"
+                        exit 7
+                    } else {
+                        Write-Log "Success: urllib3 problems appear resolved; continuing." "INFO"
+                    }
+                } else {
+                    Write-Log "Aborting bootstrap to avoid leaving a broken environment." "ERROR"
+                    exit 7
+                }
+            }
         }
     } catch {
         Write-Log "Failed to run environment verification: $_" "ERROR"
diff --git a/scripts/bootstrap.sh b/scripts/bootstrap.sh
index 07890e4..28f585e 100644
--- a/scripts/bootstrap.sh
+++ b/scripts/bootstrap.sh
@@ -24,11 +24,39 @@ PYTHON_CMD=""
 NOINSTALL=false
 FORCE=false
 QUIET=false
+FIX_URLLIB3=false
 # Playwright options
 PLAYWRIGHT_BROWSERS="chromium"   # comma-separated (chromium,firefox,webkit) or 'all'
 NO_PLAYWRIGHT=false
 
-usage() {
+attempt_fix_urllib3() {
+  local venv_py="$1"
+  echo "Attempting automatic urllib3 fix in venv: $venv_py" >&2
+  # Temporarily disable set -e to inspect return codes ourselves
+  set +e
+  "$venv_py" -m pip uninstall urllib3-future -y >/dev/null 2>&1 || true
+  "$venv_py" -m pip install --upgrade --force-reinstall urllib3
+  local pip_ret=$?
+  # Best-effort install/update for niquests; non-fatal
+  "$venv_py" -m pip install niquests -U >/dev/null 2>&1 || true
+  set -e
+
+  if [[ $pip_ret -ne 0 ]]; then
+    echo "ERROR: pip failed to reinstall urllib3 (exit $pip_ret)" >&2
+    return 2
+  fi
+
+  # Verify fix
+  if "$venv_py" -c 'from SYS.env_check import check_urllib3_compat; ok,msg = check_urllib3_compat(); import sys; sys.exit(0 if ok else 2)'; then
+    echo "Success: urllib3 issues resolved" >&2
+    return 0
+  fi
+
+  echo "ERROR: urllib3 fix attempt incomplete (import check failed)" >&2
+  return 3
+}
+
+usage() { 
   cat <<EOF
 Usage: $0 [options]
 Options:
@@ -40,6 +68,7 @@ Options:
   --no-playwright       Skip installing Playwright browsers (default: install chromium)
   --playwright-browsers <list>  Comma-separated list of browsers to install (default: chromium)
   -q, --quiet           Quiet / non-interactive mode; abort on errors instead of prompting
+  -F, --fix-urllib3     Attempt to automatically fix known urllib3 issues in the venv if detected
   -f, --force           Overwrite existing venv without prompting
   -h, --help            Show this help
 EOF
@@ -53,6 +82,7 @@ while [[ $# -gt 0 ]]; do
     -d|--desktop) DESKTOP=true; shift;;
     -n|--no-install) NOINSTALL=true; shift;;
     -f|--force) FORCE=true; shift;;
+    -F|--fix-urllib3) FIX_URLLIB3=true; shift;;
     -q|--quiet) QUIET=true; shift;;
     -h|--help) usage; exit 0;;
     --no-playwright) NO_PLAYWRIGHT=true; shift;;
@@ -172,7 +202,33 @@ if [[ "$NOINSTALL" != "true" ]]; then
     echo "  $VENV_PY -m pip uninstall urllib3-future -y" >&2
     echo "  $VENV_PY -m pip install --upgrade --force-reinstall urllib3" >&2
     echo "  $VENV_PY -m pip install niquests -U" >&2
-    exit 7
+    echo "" >&2
+    if [[ "$FIX_URLLIB3" == "true" ]]; then
+      echo "Attempting automatic fix (--fix-urllib3 requested)..." >&2
+      if attempt_fix_urllib3 "$VENV_PY"; then
+        echo "Success: urllib3 issues resolved; continuing..." >&2
+      else
+        echo "ERROR: Automatic fix did not resolve the issue; inspect .pth files in site-packages (e.g., urllib3_future.pth) and remove them, then re-run with --fix-urllib3" >&2
+        exit 7
+      fi
+    else
+      if [[ "$QUIET" == "true" ]]; then
+        echo "ERROR: Bootstrap detected a potentially broken 'urllib3' installation. Use --fix-urllib3 to attempt an automatic fix." >&2
+        exit 7
+      fi
+      read -p "Attempt automatic fix now? (y/N) " REPLY
+      if [[ "$REPLY" == "y" || "$REPLY" == "Y" ]]; then
+        if attempt_fix_urllib3 "$VENV_PY"; then
+          echo "Success: urllib3 issues resolved; continuing..." >&2
+        else
+          echo "ERROR: Automatic fix did not resolve the issue; aborting." >&2
+          exit 7
+        fi
+      else
+        echo "Aborting bootstrap. Re-run with --fix-urllib3 to attempt an automatic fix or run the commands above." >&2
+        exit 7
+      fi
+    fi
   fi
 
   # Install Playwright browsers (default: chromium) unless explicitly disabled