diff --git a/test/test-fs-wrapper.js b/test/test-fs-wrapper.js
index ed02d5756..0102829d2 100644
--- a/test/test-fs-wrapper.js
+++ b/test/test-fs-wrapper.js
@@ -405,12 +405,15 @@ async function runTests() {
     const p = path.join(TMP, 'bad.json');
     nativeFs.writeFileSync(p, '{ invalid json }');
     let threw = false;
+    let errorMessage = '';
     try {
       fs.readJsonSync(p);
-    } catch {
+    } catch (error) {
       threw = true;
+      errorMessage = error.message;
     }
     assert(threw, 'readJsonSync did not throw on invalid JSON');
+    assert(errorMessage.includes(p), 'readJsonSync error did not include file path');
   });
 
   test('readJsonSync strips UTF-8 BOM', () => {
diff --git a/tools/cli/lib/fs.js b/tools/cli/lib/fs.js
index 4e6dcfa70..6cd2c631d 100644
--- a/tools/cli/lib/fs.js
+++ b/tools/cli/lib/fs.js
@@ -166,5 +166,10 @@ module.exports.move = async function move(src, dest) {
  */
 module.exports.readJsonSync = function readJsonSync(filePath) {
   const raw = fs.readFileSync(filePath, 'utf8').replace(/^\uFEFF/, '');
-  return JSON.parse(raw);
+  try {
+    return JSON.parse(raw);
+  } catch (error) {
+    error.message = `Failed to parse JSON in ${filePath}: ${error.message}`;
+    throw error;
+  }
 };