diff --git a/sky/backends/wheel_utils.py b/sky/backends/wheel_utils.py
index 44d47b52926..ed580569e0b 100644
--- a/sky/backends/wheel_utils.py
+++ b/sky/backends/wheel_utils.py
@@ -129,7 +129,11 @@ def _build_sky_wheel() -> pathlib.Path:
 
         wheel_dir = WHEEL_DIR / hash_of_latest_wheel
         wheel_dir.mkdir(parents=True, exist_ok=True)
-        shutil.move(str(wheel_path), wheel_dir)
+        # shutil.move will fail when the file already exists and is being
+        # moved across filesystems.
+        if not os.path.exists(
+                os.path.join(wheel_dir, os.path.basename(wheel_path))):
+            shutil.move(str(wheel_path), wheel_dir)
         return wheel_dir / wheel_path.name
 
 
diff --git a/sky/utils/command_runner.py b/sky/utils/command_runner.py
index 7eae76040d8..d373df20d16 100644
--- a/sky/utils/command_runner.py
+++ b/sky/utils/command_runner.py
@@ -11,6 +11,7 @@
 from sky.skylet import constants
 from sky.skylet import log_lib
 from sky.utils import common_utils
+from sky.utils import control_master_utils
 from sky.utils import subprocess_utils
 from sky.utils import timeline
 
@@ -442,7 +443,9 @@ def __init__(
             None if ssh_control_name is None else hashlib.md5(
                 ssh_control_name.encode()).hexdigest()[:_HASH_MAX_LENGTH])
         self._ssh_proxy_command = ssh_proxy_command
-        self.disable_control_master = disable_control_master
+        self.disable_control_master = (
+            disable_control_master or
+            control_master_utils.should_disable_control_master())
         if docker_user is not None:
             assert port is None or port == 22, (
                 f'port must be None or 22 for docker_user, got {port}.')
diff --git a/sky/utils/control_master_utils.py b/sky/utils/control_master_utils.py
new file mode 100644
index 00000000000..d645014c417
--- /dev/null
+++ b/sky/utils/control_master_utils.py
@@ -0,0 +1,49 @@
+"""Utils to check if the ssh control master should be disabled."""
+
+import functools
+
+from sky import sky_logging
+from sky.utils import subprocess_utils
+
+logger = sky_logging.init_logger(__name__)
+
+
+def is_tmp_9p_filesystem() -> bool:
+    """Check if the /tmp filesystem is 9p.
+
+    Returns:
+        bool: True if the /tmp filesystem is 9p, False otherwise.
+    """
+
+    result = subprocess_utils.run(['df', '-T', '/tmp'],
+                                  capture_output=True,
+                                  text=True,
+                                  shell=None,
+                                  check=False,
+                                  executable=None)
+
+    if result.returncode != 0:
+        return False
+
+    filesystem_infos = result.stdout.strip().split('\n')
+    if len(filesystem_infos) < 2:
+        return False
+    filesystem_types = filesystem_infos[1].split()
+    if len(filesystem_types) < 2:
+        return False
+    return filesystem_types[1].lower() == '9p'
+
+
+@functools.lru_cache
+def should_disable_control_master() -> bool:
+    """Whether disable ssh control master based on file system.
+
+    Returns:
+        bool: True if the ssh control master should be disabled,
+        False otherwise.
+    """
+    if is_tmp_9p_filesystem():
+        return True
+    # there may be additional criteria to disable ssh control master
+    # in the future. They should be checked here
+    return False