diff --git a/src/env-inl.h b/src/env-inl.h
index 74e427e40353d9..9e8db822c66580 100644
--- a/src/env-inl.h
+++ b/src/env-inl.h
@@ -175,7 +175,7 @@ inline Environment::Environment(IsolateData* isolate_data,
       debugger_agent_(this),
 #if HAVE_INSPECTOR
       inspector_agent_(this),
-#endif
+#endif  // HAVE_INSPECTOR
       handle_cleanup_waiting_(0),
       http_parser_buffer_(nullptr),
       context_(context->GetIsolate(), context) {
@@ -356,6 +356,29 @@ inline IsolateData* Environment::isolate_data() const {
   return isolate_data_;
 }
 
+#if HAVE_INSPECTOR
+inline void Environment::ContextCreated(node::inspector::ContextInfo* info) {
+  contexts()->push_back(info);
+  if (inspector_agent()->IsStarted()) {
+    inspector_agent()->ContextCreated(info);
+  }
+}
+inline void Environment::ContextDestroyed(v8::Local<v8::Context> context) {
+  for (auto i = std::begin(*contexts()); i != std::end(*contexts()); ++i) {
+    auto it = *i;
+    if (it->context(isolate()) == context) {
+      delete it;
+      contexts()->erase(i);
+      if (inspector_agent()->IsStarted()) {
+          inspector_agent()->ContextDestroyed(context);
+      }
+      return;
+    }
+  }
+}
+
+#endif  // HAVE_INSPECTOR
+
 inline void Environment::ThrowError(const char* errmsg) {
   ThrowError(v8::Exception::Error, errmsg);
 }
diff --git a/src/env.cc b/src/env.cc
index efa2d53f0435b2..ec94e98e645582 100644
--- a/src/env.cc
+++ b/src/env.cc
@@ -12,6 +12,10 @@
 
 #include <stdio.h>
 
+#if HAVE_INSPECTOR
+#include "inspector_agent.h"
+#endif
+
 namespace node {
 
 using v8::Context;
@@ -30,6 +34,11 @@ void Environment::Start(int argc,
   HandleScope handle_scope(isolate());
   Context::Scope context_scope(context());
 
+#if HAVE_INSPECTOR
+  ContextCreated(
+      new node::inspector::ContextInfo(context(), 1, "NodeJS Main Context"));
+#endif
+
   uv_check_init(event_loop(), immediate_check_handle());
   uv_unref(reinterpret_cast<uv_handle_t*>(immediate_check_handle()));
 
diff --git a/src/env.h b/src/env.h
index fe49ac0c876a47..77d46c1c6912cc 100644
--- a/src/env.h
+++ b/src/env.h
@@ -7,6 +7,7 @@
 #include "debug-agent.h"
 #if HAVE_INSPECTOR
 #include "inspector_agent.h"
+#include <vector>
 #endif
 #include "handle_wrap.h"
 #include "req-wrap.h"
@@ -528,6 +529,12 @@ class Environment {
   inline inspector::Agent* inspector_agent() {
     return &inspector_agent_;
   }
+
+  inline void ContextCreated(node::inspector::ContextInfo* info);
+  inline void ContextDestroyed(v8::Local<v8::Context> context);
+  inline std::vector<node::inspector::ContextInfo*>* contexts() {
+    return &contexts_;
+  }
 #endif
 
   typedef ListHead<HandleWrap, &HandleWrap::handle_wrap_queue_> HandleWrapQueue;
@@ -564,6 +571,7 @@ class Environment {
   debugger::Agent debugger_agent_;
 #if HAVE_INSPECTOR
   inspector::Agent inspector_agent_;
+  std::vector<node::inspector::ContextInfo*> contexts_;
 #endif
 
   HandleWrapQueue handle_wrap_queue_;
diff --git a/src/inspector_agent.cc b/src/inspector_agent.cc
index 3f3d548de4cdf6..ffca94a839751a 100644
--- a/src/inspector_agent.cc
+++ b/src/inspector_agent.cc
@@ -191,6 +191,8 @@ class AgentImpl {
   bool Start(v8::Platform* platform, const char* path, int port, bool wait);
   // Stop the inspector agent
   void Stop();
+  void ContextCreated(const node::inspector::ContextInfo* info);
+  void ContextDestroyed(v8::Local<v8::Context> context);
 
   bool IsStarted();
   bool IsConnected() {  return state_ == State::kConnected; }
@@ -323,8 +325,22 @@ class V8NodeInspector : public v8_inspector::V8InspectorClient {
                     terminated_(false),
                     running_nested_loop_(false),
                     inspector_(V8Inspector::create(env->isolate(), this)) {
-    inspector_->contextCreated(
-        v8_inspector::V8ContextInfo(env->context(), 1, "NodeJS Main Context"));
+    v8::HandleScope handles(env_->isolate());
+    for (auto it : *env->contexts()) {
+      contextCreated(it);
+    }
+  }
+
+  void contextCreated(const node::inspector::ContextInfo* info) {
+    inspector()->contextCreated(
+        v8_inspector::V8ContextInfo(
+          info->context(env_->isolate()),
+          info->groupId(),
+          info->name()));
+  }
+
+  void contextDestroyed(v8::Local<v8::Context> context) {
+    inspector()->contextDestroyed(context);
   }
 
   void runMessageLoopOnPause(int context_group_id) override {
@@ -510,6 +526,13 @@ void AgentImpl::Stop() {
   delete inspector_;
 }
 
+void AgentImpl::ContextCreated(const node::inspector::ContextInfo* info) {
+  inspector_->contextCreated(info);
+}
+void AgentImpl::ContextDestroyed(v8::Local<v8::Context> context) {
+  inspector_->contextDestroyed(context);
+}
+
 bool AgentImpl::IsStarted() {
   return !!platform_;
 }
@@ -865,6 +888,13 @@ void Agent::Stop() {
   impl->Stop();
 }
 
+void Agent::ContextCreated(const node::inspector::ContextInfo* info) {
+  impl->ContextCreated(info);
+}
+void Agent::ContextDestroyed(v8::Local<v8::Context> context) {
+  impl->ContextDestroyed(context);
+}
+
 bool Agent::IsStarted() {
   return impl->IsStarted();
 }
diff --git a/src/inspector_agent.h b/src/inspector_agent.h
index 3607cffba5d21f..8667ab664bf038 100644
--- a/src/inspector_agent.h
+++ b/src/inspector_agent.h
@@ -5,6 +5,8 @@
 #error("This header can only be used when inspector is enabled")
 #endif
 
+#include "platform/v8_inspector/public/V8Inspector.h"
+
 // Forward declaration to break recursive dependency chain with src/env.h.
 namespace node {
 class Environment;
@@ -23,6 +25,25 @@ namespace inspector {
 
 class AgentImpl;
 
+class ContextInfo {
+ public:
+  explicit ContextInfo(v8::Local<v8::Context> context, const int groupId,
+                       const char* name)
+                       : group_id_(groupId),
+                       name_(name) {
+                       context_.Reset(context->GetIsolate(), context);
+  }
+  inline v8::Local<v8::Context> context(v8::Isolate* isolate) const {
+    return context_.Get(isolate);
+  }
+  int groupId() const { return group_id_; }
+  const char* name() const { return name_; }
+ private:
+  v8::Persistent<v8::Context> context_;
+  const int group_id_;
+  const char* name_;
+};
+
 class Agent {
  public:
   explicit Agent(node::Environment* env);
@@ -33,6 +54,9 @@ class Agent {
   // Stop the inspector agent
   void Stop();
 
+  void ContextCreated(const ContextInfo* info);
+  void ContextDestroyed(v8::Local<v8::Context> context);
+
   bool IsStarted();
   bool IsConnected();
   void WaitForDisconnect();
diff --git a/src/node_contextify.cc b/src/node_contextify.cc
index d74b01ea0da371..29ad29947925d0 100644
--- a/src/node_contextify.cc
+++ b/src/node_contextify.cc
@@ -9,6 +9,10 @@
 #include "util-inl.h"
 #include "v8-debug.h"
 
+#if HAVE_INSPECTOR
+#include "inspector_agent.h"
+#endif
+
 namespace node {
 
 using v8::Array;
@@ -207,6 +211,10 @@ class ContextifyContext {
     object_template->SetHandler(config);
 
     Local<Context> ctx = Context::New(env->isolate(), nullptr, object_template);
+#if HAVE_INSPECTOR
+    env->ContextCreated(
+        new node::inspector::ContextInfo(ctx, 1, "vm Module Context"));
+#endif
 
     if (ctx.IsEmpty()) {
       env->ThrowError("Could not instantiate context");
@@ -323,6 +331,9 @@ class ContextifyContext {
 
   static void WeakCallback(const WeakCallbackInfo<ContextifyContext>& data) {
     ContextifyContext* context = data.GetParameter();
+#if HAVE_INSPECTOR
+    context->env()->ContextDestroyed(context->context());
+#endif
     delete context;
   }