diff --git a/overrides/path/node b/overrides/path/node
index ee1061ca..a19c5c18 100755
--- a/overrides/path/node
+++ b/overrides/path/node
@@ -36,9 +36,21 @@ PATH="$SCRIPT_DIR:$PATH"
 # Define the path to our helper script using the reliable SCRIPT_DIR
 PREPEND_PATH="$SCRIPT_DIR/../js/prepend-node.js"
 
-# Call node with the given arguments, prefixed with our extra logic
-if command -v winpty >/dev/null 2>&1; then
-    winpty "$real_node" -r "$PREPEND_PATH" "$@"
-else
-    "$real_node" -r "$PREPEND_PATH" "$@"
-fi
\ No newline at end of file
+case "$NODE_OPTIONS" in
+  *"$HTTP_TOOLKIT_OVERRIDE_PATH"*)
+    # If our config is already inside NODE_OPTIONS, we don't need to do anything:
+    if command -v winpty >/dev/null 2>&1; then
+        winpty "$real_node" "$@"
+    else
+        "$real_node" "$@"
+    fi
+    ;;
+  *)
+    # Otherwise, we need to inject --require $PREPEND into the node CLI:
+    if command -v winpty >/dev/null 2>&1; then
+        winpty "$real_node" --require "$PREPEND_PATH" "$@"
+    else
+        "$real_node" --require "$PREPEND_PATH" "$@"
+    fi
+    ;;
+esac
\ No newline at end of file
diff --git a/overrides/path/node.bat b/overrides/path/node.bat
index 54f32247..c3d6ac26 100755
--- a/overrides/path/node.bat
+++ b/overrides/path/node.bat
@@ -7,10 +7,23 @@ set WRAPPER_FOLDER=%HTTP_TOOLKIT_OVERRIDE_PATH%\path
 call set PATH=%%PATH:%WRAPPER_FOLDER%;=%%
 
 REM Get the real node path, store it in %REAL_NODE%
-FOR /F "tokens=*" %%g IN ('where node') do (SET REAL_NODE=%%g)
+FOR /F "tokens=*" %%g IN ('where node') do (
+    SET REAL_NODE=%%g
+    GOTO :Break
+)
+:Break
 
 REM Reset PATH, so its visible to node & subprocesses
 set PATH=%ORIGINALPATH%
 
-REM Start Node for real, with an extra arg to inject our logic
-"%REAL_NODE%" -r "%WRAPPER_FOLDER%\..\js\prepend-node.js" %*
\ No newline at end of file
+REM Check if our config is already inside NODE_OPTIONS, if so then we don't actually
+REM need to do anything.
+REM NODE_OPTIONS includes forward slash paths even on Windows for some reason, so
+REM check for that instead.
+set "OVERRIDE_PATH_POSIX=%HTTP_TOOLKIT_OVERRIDE_PATH:\=/%"
+echo "%NODE_OPTIONS%" | findstr /C:"%OVERRIDE_PATH_POSIX%" >nul 2>&1
+if %errorlevel% equ 0 (
+    "%REAL_NODE%" %*
+) else (
+    "%REAL_NODE%" --require "%WRAPPER_FOLDER%\..\js\prepend-node.js" %*
+)
\ No newline at end of file