diff --git a/src/resources/extensions/gsd/auto-tool-tracking.ts b/src/resources/extensions/gsd/auto-tool-tracking.ts
index 9e7ffc049..cab495813 100644
--- a/src/resources/extensions/gsd/auto-tool-tracking.ts
+++ b/src/resources/extensions/gsd/auto-tool-tracking.ts
@@ -92,7 +92,7 @@ export function clearInFlightTools(): void {
  * handler. When these errors occur, retrying the same unit will produce the same
  * failure, so the retry loop must be broken.
  */
-const TOOL_INVOCATION_ERROR_RE = /Validation failed for tool|Expected ',' or '\}' in JSON|Unexpected end of JSON|Unexpected token.*in JSON/i;
+const TOOL_INVOCATION_ERROR_RE = /Validation failed for tool|Expected ',' or '\}'(?: after property value)?(?: in JSON)?|Unexpected end of JSON|Unexpected token.*in JSON/i;
 
 /**
  * Returns true if the error message indicates a tool invocation failure due to
diff --git a/src/resources/extensions/gsd/tests/tool-invocation-error-loop-break.test.ts b/src/resources/extensions/gsd/tests/tool-invocation-error-loop-break.test.ts
index 5a2cdfa58..c802e91a5 100644
--- a/src/resources/extensions/gsd/tests/tool-invocation-error-loop-break.test.ts
+++ b/src/resources/extensions/gsd/tests/tool-invocation-error-loop-break.test.ts
@@ -61,6 +61,13 @@ describe("#2883: isToolInvocationError classification", () => {
     );
   });
 
+  test("detects Node v18+ JSON parse variant with property-value text", () => {
+    assert.equal(
+      isToolInvocationError("Expected ',' or '}' after property value in JSON at position 4096"),
+      true,
+    );
+  });
+
   test("detects Unexpected end of JSON input", () => {
     assert.equal(
       isToolInvocationError("Unexpected end of JSON input"),