diff --git a/src/bun.js/bindings/BunDebugger.cpp b/src/bun.js/bindings/BunDebugger.cpp
index 5ba768ab75..d2aa9ef4c1 100644
--- a/src/bun.js/bindings/BunDebugger.cpp
+++ b/src/bun.js/bindings/BunDebugger.cpp
@@ -136,6 +136,10 @@ public:
         // StopTheWorld (JSC's JSON parser needs GC heap operations that conflict with STW).
         // By attaching early, we enable the pause mechanism so messages can be
         // dispatched in the normal runWhilePaused loop after STW completes.
+        // Pre-attach the debugger so that notifyNeedDebuggerBreak() can trigger a pause
+        // for CDP message dispatch. This only fires on the SIGUSR1 path because --inspect
+        // and --inspect-wait already have the debugger attached by JSC at startup
+        // (globalObject->debugger() is non-null), so the condition is false for those paths.
         auto* controllerDebugger = globalObject->inspectorController().debugger();
         if (controllerDebugger && !globalObject->debugger()) {
             controllerDebugger->attach(globalObject);
diff --git a/test/js/bun/runtime-inspector/runtime-inspector-windows.test.ts b/test/js/bun/runtime-inspector/runtime-inspector-windows.test.ts
index 90bc992d98..8f99817707 100644
--- a/test/js/bun/runtime-inspector/runtime-inspector-windows.test.ts
+++ b/test/js/bun/runtime-inspector/runtime-inspector-windows.test.ts
@@ -93,7 +93,7 @@ describe.skipIf(!isWindows)("Runtime inspector Windows file mapping", () => {
 
     // Verify inspector actually started
     expect(targetStderr).toContain("Bun Inspector");
-    expect(targetStderr).toContain("ws://localhost:6499/");
+    expect(targetStderr).toMatch(/ws:\/\/localhost:\d+\//);
   });
 
   test("_debugProcess works with current process's own pid", async () => {