diff --git a/sky/backends/cloud_vm_ray_backend.py b/sky/backends/cloud_vm_ray_backend.py
index f3d855d479b..7f490743f8b 100644
--- a/sky/backends/cloud_vm_ray_backend.py
+++ b/sky/backends/cloud_vm_ray_backend.py
@@ -150,6 +150,18 @@
 _MAX_INLINE_SCRIPT_LENGTH = 120 * 1024
 
 
+def _is_command_length_over_limit(command: str) -> bool:
+    """Check if the length of the command exceeds the limit.
+
+    We calculate the length of the command after quoting the command twice as
+    when it is executed by the CommandRunner, the command will be quoted twice
+    to ensure the correctness, which will add significant length to the command.
+    """
+
+    quoted_length = len(shlex.quote(shlex.quote(command)))
+    return quoted_length > _MAX_INLINE_SCRIPT_LENGTH
+
+
 def _get_cluster_config_template(cloud):
     cloud_to_template = {
         clouds.AWS: 'aws-ray.yml.j2',
@@ -3159,8 +3171,7 @@ def _setup_node(node_id: int) -> None:
             setup_script = log_lib.make_task_bash_script(setup,
                                                          env_vars=setup_envs)
             encoded_script = shlex.quote(setup_script)
-            if (detach_setup or
-                    len(encoded_script) > _MAX_INLINE_SCRIPT_LENGTH):
+            if detach_setup or _is_command_length_over_limit(encoded_script):
                 with tempfile.NamedTemporaryFile('w', prefix='sky_setup_') as f:
                     f.write(setup_script)
                     f.flush()
@@ -3271,7 +3282,7 @@ def _exec_code_on_head(
 
         code = job_lib.JobLibCodeGen.queue_job(job_id, job_submit_cmd)
         job_submit_cmd = ' && '.join([mkdir_code, create_script_code, code])
-        if len(job_submit_cmd) > _MAX_INLINE_SCRIPT_LENGTH:
+        if _is_command_length_over_limit(job_submit_cmd):
             runners = handle.get_command_runners()
             head_runner = runners[0]
             with tempfile.NamedTemporaryFile('w', prefix='sky_app_') as fp: