diff --git a/dist/hpl-toolbox-0.1.7.exe b/dist/hpl-toolbox-0.1.7.exe
index 3ca27a5..d89ff8e 100644
Binary files a/dist/hpl-toolbox-0.1.7.exe and b/dist/hpl-toolbox-0.1.7.exe differ
diff --git a/dist/hpl-toolbox-0.1.7.vsix b/dist/hpl-toolbox-0.1.7.vsix
index bc8aaba..2a6cd12 100644
Binary files a/dist/hpl-toolbox-0.1.7.vsix and b/dist/hpl-toolbox-0.1.7.vsix differ
diff --git a/src/tools/playworksConverter.ts b/src/tools/playworksConverter.ts
index c766e82..5484728 100644
--- a/src/tools/playworksConverter.ts
+++ b/src/tools/playworksConverter.ts
@@ -546,6 +546,10 @@ ${getToolWebviewStyles()}
     convertBtn.disabled = !srcEl.value || !outEl.value || !baseNameEl.value.trim() || !hasNet;
   }
 
+  function defaultOutputDir(dir) {
+    return dir ? dir.replace(/[\\\\/]+$/, '') + '\\\\Output' : '';
+  }
+
   document.getElementById('pickSrc').addEventListener('click', () => vscode.postMessage({ type: 'pickSource' }));
   document.getElementById('pickOut').addEventListener('click', () => vscode.postMessage({ type: 'pickOutput' }));
   document.getElementById('selectAll').addEventListener('click', () => {
@@ -596,8 +600,8 @@ ${getToolWebviewStyles()}
       srcNameEl.textContent = msg.path.split(/[\\\\/]/).filter(Boolean).pop() || msg.path;
       baseNameEl.value = msg.baseName || '';
       if (!outEl.value && msg.dir) {
-        outEl.value = msg.dir;
-        outputDir = msg.dir;
+        outEl.value = defaultOutputDir(msg.dir);
+        outputDir = outEl.value;
       }
       updateConvertBtn();
     } else if (msg.type === 'outputPicked') {
diff --git a/standalone/playworks.go b/standalone/playworks.go
index 2155d85..2cd77ff 100644
--- a/standalone/playworks.go
+++ b/standalone/playworks.go
@@ -161,11 +161,15 @@ function renderSourceSelection() {
 function setSource(path, baseName, dir) {
   srcEl.value = path || '';
   baseNameEl.value = baseName || '';
-  if (!outEl.value && dir) { outEl.value = dir.replace(/[\\\/]+$/, '') + '\\\\Output'; outputDir = outEl.value; }
+  if (!outEl.value && dir) { outEl.value = defaultOutputDir(dir); outputDir = outEl.value; }
   renderSourceSelection();
   updateConvertBtn();
 }
 
+function defaultOutputDir(dir) {
+  return dir ? dir.replace(/[\\\/]+$/, '') + '\\Output' : '';
+}
+
 function clearSource() {
   srcEl.value = '';
   baseNameEl.value = '';