diff --git a/src/env-inl.h b/src/env-inl.h
index b476b02ddc..5372c34a92 100644
--- a/src/env-inl.h
+++ b/src/env-inl.h
@@ -293,7 +293,6 @@ inline Environment::Environment(IsolateData* isolate_data,
 #if HAVE_INSPECTOR
       inspector_agent_(this),
 #endif
-      handle_cleanup_waiting_(0),
       http_parser_buffer_(nullptr),
       fs_stats_field_array_(nullptr),
       context_(context->GetIsolate(), context) {
@@ -397,6 +396,15 @@ inline void Environment::CloseHandle(T* handle, OnCloseCallback callback) {
   });
 }
 
+void Environment::IncreaseWaitingRequestCounter() {
+  request_waiting_++;
+}
+
+void Environment::DecreaseWaitingRequestCounter() {
+  request_waiting_--;
+  CHECK_GE(request_waiting_, 0);
+}
+
 inline uv_loop_t* Environment::event_loop() const {
   return isolate_data()->event_loop();
 }
diff --git a/src/env.cc b/src/env.cc
index 91db0f43e6..79c819708d 100644
--- a/src/env.cc
+++ b/src/env.cc
@@ -103,8 +103,11 @@ void Environment::CleanupHandles() {
     delete hc;
   }
 
-  while (handle_cleanup_waiting_ != 0 || !handle_wrap_queue_.IsEmpty())
+  while (handle_cleanup_waiting_ != 0 ||
+         request_waiting_ != 0 ||
+         !handle_wrap_queue_.IsEmpty()) {
     uv_run(event_loop(), UV_RUN_ONCE);
+  }
 }
 
 void Environment::StartProfilerIdleNotifier() {
diff --git a/src/env.h b/src/env.h
index 2dab4dfcaf..83efcd08d1 100644
--- a/src/env.h
+++ b/src/env.h
@@ -562,6 +562,9 @@ class Environment {
   template <typename T, typename OnCloseCallback>
   inline void CloseHandle(T* handle, OnCloseCallback callback);
 
+  inline void IncreaseWaitingRequestCounter();
+  inline void DecreaseWaitingRequestCounter();
+
   inline AsyncHooks* async_hooks();
   inline DomainFlag* domain_flag();
   inline TickInfo* tick_info();
@@ -724,7 +727,8 @@ class Environment {
   ReqWrapQueue req_wrap_queue_;
   ListHead<HandleCleanup,
            &HandleCleanup::handle_cleanup_queue_> handle_cleanup_queue_;
-  int handle_cleanup_waiting_;
+  int handle_cleanup_waiting_ = 0;
+  int request_waiting_ = 0;
 
   double* heap_statistics_buffer_ = nullptr;
   double* heap_space_statistics_buffer_ = nullptr;
diff --git a/src/node_api.cc b/src/node_api.cc
index 93c218bece..efe0267dc4 100644
--- a/src/node_api.cc
+++ b/src/node_api.cc
@@ -3382,6 +3382,9 @@ class Work : public node::AsyncResource {
       // Establish a handle scope here so that every callback doesn't have to.
       // Also it is needed for the exception-handling below.
       v8::HandleScope scope(env->isolate);
+      auto env_ = node::Environment::GetCurrent(env->isolate);
+      env_->DecreaseWaitingRequestCounter();
+
       CallbackScope callback_scope(work);
 
       work->_complete(env, ConvertUVErrorCode(status), work->_data);
@@ -3470,13 +3473,12 @@ napi_status napi_queue_async_work(napi_env env, napi_async_work work) {
   CHECK_ARG(env, work);
 
   // Consider: Encapsulate the uv_loop_t into an opaque pointer parameter.
-  // Currently the environment event loop is the same as the UV default loop.
-  // Someday (if node ever supports multiple isolates), it may be better to get
-  // the loop from node::Environment::GetCurrent(env->isolate)->event_loop();
-  uv_loop_t* event_loop = uv_default_loop();
+  auto env_ = node::Environment::GetCurrent(env->isolate);
+  uv_loop_t* event_loop = env_->event_loop();
 
   uvimpl::Work* w = reinterpret_cast<uvimpl::Work*>(work);
 
+  env_->IncreaseWaitingRequestCounter();
   CALL_UV(env, uv_queue_work(event_loop,
                              w->Request(),
                              uvimpl::Work::ExecuteCallback,
diff --git a/src/node_crypto.cc b/src/node_crypto.cc
index 0482bce527..9bdb02fe96 100644
--- a/src/node_crypto.cc
+++ b/src/node_crypto.cc
@@ -5272,8 +5272,13 @@ void PBKDF2Request::After() {
 
 
 void PBKDF2Request::After(uv_work_t* work_req, int status) {
-  CHECK_EQ(status, 0);
   PBKDF2Request* req = ContainerOf(&PBKDF2Request::work_req_, work_req);
+  req->env()->DecreaseWaitingRequestCounter();
+  if (status == UV_ECANCELED) {
+    delete req;
+    return;
+  }
+  CHECK_EQ(status, 0);
   req->After();
   delete req;
 }
@@ -5380,6 +5385,7 @@ void PBKDF2(const FunctionCallbackInfo<Value>& args) {
           .FromJust();
     }
 
+    env->IncreaseWaitingRequestCounter();
     uv_queue_work(env->event_loop(),
                   req->work_req(),
                   PBKDF2Request::Work,
@@ -5532,10 +5538,15 @@ void RandomBytesCheck(RandomBytesRequest* req, Local<Value> (*argv)[2]) {
 
 
 void RandomBytesAfter(uv_work_t* work_req, int status) {
-  CHECK_EQ(status, 0);
   RandomBytesRequest* req =
       ContainerOf(&RandomBytesRequest::work_req_, work_req);
   Environment* env = req->env();
+  env->DecreaseWaitingRequestCounter();
+  if (status == UV_ECANCELED) {
+    delete req;
+    return;
+  }
+  CHECK_EQ(status, 0);
   HandleScope handle_scope(env->isolate());
   Context::Scope context_scope(env->context());
   Local<Value> argv[2];
@@ -5589,6 +5600,7 @@ void RandomBytes(const FunctionCallbackInfo<Value>& args) {
           .FromJust();
     }
 
+    env->IncreaseWaitingRequestCounter();
     uv_queue_work(env->event_loop(),
                   req->work_req(),
                   RandomBytesWork,
@@ -5635,6 +5647,7 @@ void RandomBytesBuffer(const FunctionCallbackInfo<Value>& args) {
           .FromJust();
     }
 
+    env->IncreaseWaitingRequestCounter();
     uv_queue_work(env->event_loop(),
                   req->work_req(),
                   RandomBytesWork,
diff --git a/src/node_zlib.cc b/src/node_zlib.cc
index fdfd314222..b7283c5639 100644
--- a/src/node_zlib.cc
+++ b/src/node_zlib.cc
@@ -219,6 +219,7 @@ class ZCtx : public AsyncWrap {
     }
 
     // async version
+    env->IncreaseWaitingRequestCounter();
     uv_queue_work(env->event_loop(), work_req, ZCtx::Process, ZCtx::After);
   }
 
@@ -366,10 +367,17 @@ class ZCtx : public AsyncWrap {
 
   // v8 land!
   static void After(uv_work_t* work_req, int status) {
-    CHECK_EQ(status, 0);
-
     ZCtx* ctx = ContainerOf(&ZCtx::work_req_, work_req);
     Environment* env = ctx->env();
+    ctx->write_in_progress_ = false;
+
+    env->DecreaseWaitingRequestCounter();
+    if (status == UV_ECANCELED) {
+      ctx->Close();
+      return;
+    }
+
+    CHECK_EQ(status, 0);
 
     HandleScope handle_scope(env->isolate());
     Context::Scope context_scope(env->context());
@@ -379,7 +387,6 @@ class ZCtx : public AsyncWrap {
 
     ctx->write_result_[0] = ctx->strm_.avail_out;
     ctx->write_result_[1] = ctx->strm_.avail_in;
-    ctx->write_in_progress_ = false;
 
     // call the write() cb
     Local<Function> cb = PersistentToLocal(env->isolate(),
diff --git a/src/req-wrap-inl.h b/src/req-wrap-inl.h
index 5745ec2692..5838ad1b9b 100644
--- a/src/req-wrap-inl.h
+++ b/src/req-wrap-inl.h
@@ -110,6 +110,7 @@ struct MakeLibuvRequestCallback<ReqT, void(*)(ReqT*, Args...)> {
 
   static void Wrapper(ReqT* req, Args... args) {
     ReqWrap<ReqT>* req_wrap = ContainerOf(&ReqWrap<ReqT>::req_, req);
+    req_wrap->env()->DecreaseWaitingRequestCounter();
     T original_callback = reinterpret_cast<T>(req_wrap->original_callback_);
     original_callback(req, args...);
   }
@@ -126,6 +127,7 @@ template <typename T>
 template <typename LibuvFunction, typename... Args>
 int ReqWrap<T>::Dispatch(LibuvFunction fn, Args... args) {
   Dispatched();
+  env()->IncreaseWaitingRequestCounter();
 
   // This expands as:
   //