diff --git a/python/ray/monitor.py b/python/ray/monitor.py
index 722ff8b846c8..8f18250d22de 100644
--- a/python/ray/monitor.py
+++ b/python/ray/monitor.py
@@ -13,6 +13,7 @@
 import ray.ray_constants as ray_constants
 from ray.utils import binary_to_hex, setup_logger
 from ray.autoscaler.commands import teardown_cluster
+import redis
 
 logger = logging.getLogger(__name__)
 
@@ -161,7 +162,11 @@ def process_messages(self, max_messages=10000):
         subscribe_clients = [self.primary_subscribe_client]
         for subscribe_client in subscribe_clients:
             for _ in range(max_messages):
-                message = subscribe_client.get_message()
+                message = None
+                try:
+                    message = subscribe_client.get_message()
+                except redis.exceptions.ConnectionError:
+                    pass
                 if message is None:
                     # Continue on to the next subscribe client.
                     break
diff --git a/src/ray/core_worker/core_worker.cc b/src/ray/core_worker/core_worker.cc
index 9cba80710d50..74690e67d66f 100644
--- a/src/ray/core_worker/core_worker.cc
+++ b/src/ray/core_worker/core_worker.cc
@@ -152,6 +152,11 @@ void CoreWorkerProcess::EnsureInitialized() {
 CoreWorker &CoreWorkerProcess::GetCoreWorker() {
   EnsureInitialized();
   if (instance_->options_.num_workers == 1) {
+    // TODO(mehrdadn): Remove this when the bug is resolved.
+    // Somewhat consistently reproducible via
+    // python/ray/tests/test_basic.py::test_background_tasks_with_max_calls
+    // with -c opt on Windows.
+    RAY_CHECK(instance_->global_worker_) << "global_worker_ must not be NULL";
     return *instance_->global_worker_;
   }
   auto ptr = current_core_worker_.lock();
diff --git a/src/ray/gcs/asio.cc b/src/ray/gcs/asio.cc
index f22165fd942e..8e71fb83869c 100644
--- a/src/ray/gcs/asio.cc
+++ b/src/ray/gcs/asio.cc
@@ -79,7 +79,8 @@ void RedisAsioClient::operate() {
 
 void RedisAsioClient::handle_read(boost::system::error_code error_code) {
   RAY_CHECK(!error_code || error_code == boost::asio::error::would_block ||
-            error_code == boost::asio::error::connection_reset);
+            error_code == boost::asio::error::connection_reset)
+      << "handle_read(error_code = " << error_code << ")";
   read_in_progress_ = false;
   redis_async_context_.RedisAsyncHandleRead();
 
@@ -90,7 +91,8 @@ void RedisAsioClient::handle_read(boost::system::error_code error_code) {
 
 void RedisAsioClient::handle_write(boost::system::error_code error_code) {
   RAY_CHECK(!error_code || error_code == boost::asio::error::would_block ||
-            error_code == boost::asio::error::connection_reset);
+            error_code == boost::asio::error::connection_reset)
+      << "handle_write(error_code = " << error_code << ")";
   write_in_progress_ = false;
   redis_async_context_.RedisAsyncHandleWrite();
 
diff --git a/src/ray/gcs/redis_async_context.cc b/src/ray/gcs/redis_async_context.cc
index 5af88cc6db69..33f388684222 100644
--- a/src/ray/gcs/redis_async_context.cc
+++ b/src/ray/gcs/redis_async_context.cc
@@ -50,7 +50,11 @@ void RedisAsyncContext::RedisAsyncHandleRead() {
   // This function will execute the callbacks which are registered by
   // `redisvAsyncCommand`, `redisAsyncCommandArgv` and so on.
   std::lock_guard<std::mutex> lock(mutex_);
-
+  // TODO(mehrdadn): Remove this when the bug is resolved.
+  // Somewhat consistently reproducible via
+  // python/ray/tests/test_basic.py::test_background_tasks_with_max_calls
+  // with -c opt on Windows.
+  RAY_CHECK(redis_async_context_) << "redis_async_context_ must not be NULL here";
   redisAsyncHandleRead(redis_async_context_);
 }