diff --git a/python/ray/tests/test_runtime_env_working_dir.py b/python/ray/tests/test_runtime_env_working_dir.py
index 889cb958f..93e203c26 100644
--- a/python/ray/tests/test_runtime_env_working_dir.py
+++ b/python/ray/tests/test_runtime_env_working_dir.py
@@ -72,17 +72,24 @@ def test_lazy_reads(start_cluster, tmp_working_dir, option: str):
     """
     cluster, address = start_cluster
 
-    if option == "failure":
-        # Don't pass the files at all, so it should fail!
-        ray.init(address)
-    elif option == "working_dir":
-        ray.init(address, runtime_env={"working_dir": tmp_working_dir})
-    elif option == "py_modules":
-        ray.init(
-            address,
-            runtime_env={
-                "py_modules": [str(Path(tmp_working_dir) / "test_module")]
-            })
+    def call_ray_init():
+        if option == "failure":
+            # Don't pass the files at all, so it should fail!
+            ray.init(address)
+        elif option == "working_dir":
+            ray.init(address, runtime_env={"working_dir": tmp_working_dir})
+        elif option == "py_modules":
+            ray.init(
+                address,
+                runtime_env={
+                    "py_modules": [str(Path(tmp_working_dir) / "test_module")]
+                })
+
+    call_ray_init()
+
+    def reinit():
+        ray.shutdown()
+        call_ray_init()
 
     @ray.remote
     def test_import():
@@ -95,6 +102,8 @@ def test_lazy_reads(start_cluster, tmp_working_dir, option: str):
     else:
         assert ray.get(test_import.remote()) == 1
 
+    reinit()
+
     @ray.remote
     def test_read():
         return open("hello").read()
@@ -105,6 +114,8 @@ def test_lazy_reads(start_cluster, tmp_working_dir, option: str):
     elif option == "working_dir":
         assert ray.get(test_read.remote()) == "world"
 
+    reinit()
+
     @ray.remote
     class Actor:
         def test_import(self):
@@ -135,17 +146,26 @@ def test_captured_import(start_cluster, tmp_working_dir, option: str):
     """
     cluster, address = start_cluster
 
-    if option == "failure":
-        # Don't pass the files at all, so it should fail!
-        ray.init(address)
-    elif option == "working_dir":
-        ray.init(address, runtime_env={"working_dir": tmp_working_dir})
-    elif option == "py_modules":
-        ray.init(
-            address,
-            runtime_env={
-                "py_modules": [os.path.join(tmp_working_dir, "test_module")]
-            })
+    def call_ray_init():
+        if option == "failure":
+            # Don't pass the files at all, so it should fail!
+            ray.init(address)
+        elif option == "working_dir":
+            ray.init(address, runtime_env={"working_dir": tmp_working_dir})
+        elif option == "py_modules":
+            ray.init(
+                address,
+                runtime_env={
+                    "py_modules": [
+                        os.path.join(tmp_working_dir, "test_module")
+                    ]
+                })
+
+    call_ray_init()
+
+    def reinit():
+        ray.shutdown()
+        call_ray_init()
 
     # Import in the driver.
     sys.path.insert(0, tmp_working_dir)
@@ -161,6 +181,8 @@ def test_captured_import(start_cluster, tmp_working_dir, option: str):
     else:
         assert ray.get(test_import.remote()) == 1
 
+    reinit()
+
     @ray.remote
     class Actor:
         def test_import(self):
@@ -197,6 +219,10 @@ def test_empty_working_dir(start_cluster):
         a = A.remote()
         assert len(ray.get(a.listdir.remote())) == 0
 
+        # Test that we can reconnect with no errors
+        ray.shutdown()
+        ray.init(address, runtime_env={"working_dir": working_dir})
+
 
 @pytest.mark.parametrize("option", ["working_dir", "py_modules"])
 @pytest.mark.skipif(sys.platform == "win32", reason="Fail to create temp dir.")
diff --git a/release/.buildkite/build_pipeline.py b/release/.buildkite/build_pipeline.py
index c7d51bbcb..5faa766d8 100644
--- a/release/.buildkite/build_pipeline.py
+++ b/release/.buildkite/build_pipeline.py
@@ -189,8 +189,7 @@ NIGHTLY_TESTS = {
         "serve_cluster_fault_tolerance",
     ],
     "~/ray/release/runtime_env_tests/runtime_env_tests.yaml": [
-        "rte_many_tasks_actors",
-        "wheel_urls",
+        "rte_many_tasks_actors", "wheel_urls", "rte_ray_client"
     ],
 }
 
diff --git a/release/runtime_env_tests/workloads/rte_ray_client.py b/release/runtime_env_tests/workloads/rte_ray_client.py
index 3f4831262..d32556e72 100644
--- a/release/runtime_env_tests/workloads/rte_ray_client.py
+++ b/release/runtime_env_tests/workloads/rte_ray_client.py
@@ -69,7 +69,8 @@ if __name__ == "__main__":
 
     addr = os.environ.get("RAY_ADDRESS")
     job_name = os.environ.get("RAY_JOB_NAME", "rte_ray_client")
-    for use_working_dir in [True, False]:
+    # Test reconnecting to the same cluster multiple times.
+    for use_working_dir in [True, True, False, False]:
         with tempfile.TemporaryDirectory() as tmpdir:
             runtime_env = {"working_dir": tmpdir} if use_working_dir else None
             print("Testing with use_working_dir=" + str(use_working_dir))