diff --git a/src/ray/common/network_util.cc b/src/ray/common/network_util.cc
index a628de50f..857db87ed 100644
--- a/src/ray/common/network_util.cc
+++ b/src/ray/common/network_util.cc
@@ -13,6 +13,7 @@
 // limitations under the License.
 
 #include "network_util.h"
+
 #include "ray/util/logging.h"
 
 std::string GetValidLocalIp(int port, int64_t timeout_ms) {
@@ -71,3 +72,13 @@ bool Ping(const std::string &ip, int port, int64_t timeout_ms) {
   bool is_timeout;
   return client.Connect(ip, port, timeout_ms, &is_timeout);
 }
+
+bool CheckFree(int port) {
+  boost::asio::io_service io_service;
+  tcp::socket socket(io_service);
+  socket.open(boost::asio::ip::tcp::v4());
+  boost::system::error_code ec;
+  socket.bind(boost::asio::ip::tcp::endpoint(boost::asio::ip::tcp::v4(), port), ec);
+  socket.close();
+  return !ec.failed();
+}
diff --git a/src/ray/common/network_util.h b/src/ray/common/network_util.h
index 56776888c..a9898b87a 100644
--- a/src/ray/common/network_util.h
+++ b/src/ray/common/network_util.h
@@ -20,6 +20,7 @@
 #include <boost/bind.hpp>
 #include <boost/date_time/posix_time/posix_time_types.hpp>
 #include <boost/system/error_code.hpp>
+
 #include "constants.h"
 
 using boost::asio::deadline_timer;
@@ -123,4 +124,5 @@ std::string GetValidLocalIp(int port, int64_t timeout_ms);
 /// \return Whether target rpc server is valid.
 bool Ping(const std::string &ip, int port, int64_t timeout_ms);
 
+bool CheckFree(int port);
 #endif  // RAY_COMMON_NETWORK_UTIL_H
diff --git a/src/ray/common/ray_config_def.h b/src/ray/common/ray_config_def.h
index 92ef70650..e063217a9 100644
--- a/src/ray/common/ray_config_def.h
+++ b/src/ray/common/ray_config_def.h
@@ -116,6 +116,13 @@ RAY_CONFIG(int64_t, max_direct_call_object_size, 100 * 1024)
 // limit in Ray to avoid crashing with many small inlined task arguments.
 RAY_CONFIG(int64_t, max_grpc_message_size, 100 * 1024 * 1024)
 
+// Number of times to retry creating a gRPC server.
+RAY_CONFIG(int64_t, grpc_server_num_retries, 1)
+
+// Retry timeout for trying to create a gRPC server. Only applies if the number
+// of retries is non zero.
+RAY_CONFIG(int64_t, grpc_server_retry_timeout_milliseconds, 1000)
+
 // The min number of retries for direct actor creation tasks. The actual number
 // of creation retries will be MAX(actor_creation_min_retries, max_restarts).
 RAY_CONFIG(uint64_t, actor_creation_min_retries, 3)
diff --git a/src/ray/raylet/worker_pool.cc b/src/ray/raylet/worker_pool.cc
index ad24c9f2d..e5430979a 100644
--- a/src/ray/raylet/worker_pool.cc
+++ b/src/ray/raylet/worker_pool.cc
@@ -18,6 +18,7 @@
 #include <boost/date_time/posix_time/posix_time.hpp>
 
 #include "ray/common/constants.h"
+#include "ray/common/network_util.h"
 #include "ray/common/ray_config.h"
 #include "ray/common/status.h"
 #include "ray/gcs/pb_util.h"
@@ -296,17 +297,26 @@ Process WorkerPool::StartProcess(const std::vector<std::string> &worker_command_
 }
 
 Status WorkerPool::GetNextFreePort(int *port) {
-  if (free_ports_) {
-    if (free_ports_->empty()) {
-      return Status::Invalid(
-          "Ran out of ports to allocate to workers. Please specify a wider port range.");
-    }
+  if (!free_ports_) {
+    *port = 0;
+    return Status::OK();
+  }
+
+  // Try up to the current number of ports.
+  int current_size = free_ports_->size();
+  for (int i = 0; i < current_size; i++) {
     *port = free_ports_->front();
     free_ports_->pop();
-  } else {
-    *port = 0;
+    if (CheckFree(*port)) {
+      return Status::OK();
+    }
+    // Return to pool to check later.
+    free_ports_->push(*port);
   }
-  return Status::OK();
+  *port = -1;
+  return Status::Invalid(
+      "No available ports. Please specify a wider port range using --min-worker-port and "
+      "--max-worker-port.");
 }
 
 void WorkerPool::MarkPortAsFree(int port) {
diff --git a/src/ray/raylet/worker_pool.h b/src/ray/raylet/worker_pool.h
index 50d18cfc3..7f80fb9d5 100644
--- a/src/ray/raylet/worker_pool.h
+++ b/src/ray/raylet/worker_pool.h
@@ -261,6 +261,9 @@ class WorkerPool {
 
   /// Get the next unallocated port in the free ports list. If a port range isn't
   /// configured, returns 0.
+  /// NOTE: Ray does not 'reserve' these ports from being used by other services.
+  /// There is a race condition where another service binds to the port sometime
+  /// after this function returns and before the Worker/Driver uses the port.
   /// \param[out] port The next available port.
   Status GetNextFreePort(int *port);
 
diff --git a/src/ray/rpc/grpc_server.cc b/src/ray/rpc/grpc_server.cc
index 932ad368f..141ee426c 100644
--- a/src/ray/rpc/grpc_server.cc
+++ b/src/ray/rpc/grpc_server.cc
@@ -31,32 +31,40 @@ GrpcServer::GrpcServer(std::string name, const uint32_t port, int num_threads)
 void GrpcServer::Run() {
   uint32_t specified_port = port_;
   std::string server_address("0.0.0.0:" + std::to_string(port_));
+  int num_retries = RayConfig::instance().grpc_server_num_retries();
+  while (num_retries >= 0) {
+    grpc::ServerBuilder builder;
+    // Disable the SO_REUSEPORT option. We don't need it in ray. If the option is enabled
+    // (default behavior in grpc), we may see multiple workers listen on the same port and
+    // the requests sent to this port may be handled by any of the workers.
+    builder.AddChannelArgument(GRPC_ARG_ALLOW_REUSEPORT, 0);
+    builder.AddChannelArgument(GRPC_ARG_MAX_SEND_MESSAGE_LENGTH,
+                               RayConfig::instance().max_grpc_message_size());
+    builder.AddChannelArgument(GRPC_ARG_MAX_RECEIVE_MESSAGE_LENGTH,
+                               RayConfig::instance().max_grpc_message_size());
+    // TODO(hchen): Add options for authentication.
+    builder.AddListeningPort(server_address, grpc::InsecureServerCredentials(), &port_);
+    // Register all the services to this server.
+    if (services_.empty()) {
+      RAY_LOG(WARNING) << "No service is found when start grpc server " << name_;
+    }
+    for (auto &entry : services_) {
+      builder.RegisterService(&entry.get());
+    }
+    // Get hold of the completion queue used for the asynchronous communication
+    // with the gRPC runtime.
+    for (int i = 0; i < num_threads_; i++) {
+      cqs_[i] = builder.AddCompletionQueue();
+    }
+    // Build and start server.
+    server_ = builder.BuildAndStart();
+    if (port_ > 0) {
+      break;
+    }
+    usleep(RayConfig::instance().grpc_server_retry_timeout_milliseconds() * 1000);
+    num_retries--;
+  }
 
-  grpc::ServerBuilder builder;
-  // Disable the SO_REUSEPORT option. We don't need it in ray. If the option is enabled
-  // (default behavior in grpc), we may see multiple workers listen on the same port and
-  // the requests sent to this port may be handled by any of the workers.
-  builder.AddChannelArgument(GRPC_ARG_ALLOW_REUSEPORT, 0);
-  builder.AddChannelArgument(GRPC_ARG_MAX_SEND_MESSAGE_LENGTH,
-                             RayConfig::instance().max_grpc_message_size());
-  builder.AddChannelArgument(GRPC_ARG_MAX_RECEIVE_MESSAGE_LENGTH,
-                             RayConfig::instance().max_grpc_message_size());
-  // TODO(hchen): Add options for authentication.
-  builder.AddListeningPort(server_address, grpc::InsecureServerCredentials(), &port_);
-  // Register all the services to this server.
-  if (services_.empty()) {
-    RAY_LOG(WARNING) << "No service is found when start grpc server " << name_;
-  }
-  for (auto &entry : services_) {
-    builder.RegisterService(&entry.get());
-  }
-  // Get hold of the completion queue used for the asynchronous communication
-  // with the gRPC runtime.
-  for (int i = 0; i < num_threads_; i++) {
-    cqs_[i] = builder.AddCompletionQueue();
-  }
-  // Build and start server.
-  server_ = builder.BuildAndStart();
   // If the grpc server failed to bind the port, the `port_` will be set to 0.
   RAY_CHECK(port_ > 0)
       << "Port " << specified_port