diff --git a/lib/module.js b/lib/module.js
index aaa6220e40a25e..da8a906f951541 100644
--- a/lib/module.js
+++ b/lib/module.js
@@ -423,6 +423,10 @@ Module.prototype._compile = function(content, filename) {
 
     // Set breakpoint on module start
     if (filename === resolvedArgv) {
+      // Installing this dummy debug event listener tells V8 to start
+      // the debugger.  Without it, the setBreakPoint() fails with an
+      // 'illegal access' error.
+      global.v8debug.Debug.setListener(function() {});
       global.v8debug.Debug.setBreakPoint(compiledWrapper, 0, 0);
     }
   }
diff --git a/src/node_contextify.cc b/src/node_contextify.cc
index ae043eb376a115..e1f11c6a401b07 100644
--- a/src/node_contextify.cc
+++ b/src/node_contextify.cc
@@ -261,6 +261,12 @@ class ContextifyContext {
     if (script_source.IsEmpty())
       return;  // Exception pending.
     Local<Context> debug_context = Debug::GetDebugContext();
+    if (debug_context.IsEmpty()) {
+      // Force-load the debug context.
+      Debug::GetMirror(args.GetIsolate()->GetCurrentContext(), args[0]);
+      debug_context = Debug::GetDebugContext();
+      CHECK(!debug_context.IsEmpty());
+    }
     Environment* env = Environment::GetCurrent(args);
     ScopedEnvironment env_scope(debug_context, env);
     Context::Scope context_scope(debug_context);