diff --git a/sky/utils/command_runner.py b/sky/utils/command_runner.py
index 92d1f2749d7..09ddef0e386 100644
--- a/sky/utils/command_runner.py
+++ b/sky/utils/command_runner.py
@@ -471,7 +471,7 @@ def __init__(
         self._ssh_proxy_command = ssh_proxy_command
         self.disable_control_master = (
             disable_control_master or
-            control_master_utils.should_disable_control_master())
+            control_master_utils.should_disable_control_master(ip))
         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}.')
@@ -623,6 +623,10 @@ def run(
             else:
                 command += [f'> {log_path}']
             executable = '/bin/bash'
+        if ssh_mode == SshMode.INTERACTIVE:
+            # By default we disable stdin in run_with_log to avoid blocking, but
+            # for interactive mode, we need to enable it.
+            kwargs['stdin'] = None
         return log_lib.run_with_log(' '.join(command),
                                     log_path,
                                     require_outputs=require_outputs,
@@ -814,6 +818,10 @@ def run(
             else:
                 command += [f'> {log_path}']
             executable = '/bin/bash'
+        if ssh_mode == SshMode.INTERACTIVE:
+            # By default we disable stdin in run_with_log to avoid blocking, but
+            # for interactive mode, we need to enable it.
+            kwargs['stdin'] = None
         return log_lib.run_with_log(' '.join(command),
                                     log_path,
                                     require_outputs=require_outputs,
diff --git a/sky/utils/control_master_utils.py b/sky/utils/control_master_utils.py
index d645014c417..6798ef56be0 100644
--- a/sky/utils/control_master_utils.py
+++ b/sky/utils/control_master_utils.py
@@ -1,12 +1,19 @@
 """Utils to check if the ssh control master should be disabled."""
 
 import functools
+import subprocess
 
 from sky import sky_logging
 from sky.utils import subprocess_utils
 
 logger = sky_logging.init_logger(__name__)
 
+# The maximum number of concurrent ssh connections to a same node. This is a
+# heuristic value, based on the observation that when the number of concurrent
+# ssh connections to a node with control master is high, new connections through
+# control master will hang.
+_MAX_CONCURRENT_SSH_CONNECTIONS = 32
+
 
 def is_tmp_9p_filesystem() -> bool:
     """Check if the /tmp filesystem is 9p.
@@ -34,16 +41,53 @@ def is_tmp_9p_filesystem() -> bool:
     return filesystem_types[1].lower() == '9p'
 
 
-@functools.lru_cache
-def should_disable_control_master() -> bool:
+def should_disable_control_master(ip: str) -> bool:
     """Whether disable ssh control master based on file system.
 
+    Args:
+        ip: The ip address of the node.
+
     Returns:
         bool: True if the ssh control master should be disabled,
         False otherwise.
     """
-    if is_tmp_9p_filesystem():
+    if is_unsupported_filesystem():
+        return True
+    if is_high_concurrency(ip):
         return True
     # there may be additional criteria to disable ssh control master
     # in the future. They should be checked here
     return False
+
+
+@functools.lru_cache(maxsize=1)
+def is_unsupported_filesystem():
+    """Determine if the filesystem is unsupported."""
+    return is_tmp_9p_filesystem()
+
+
+def is_high_concurrency(ip: str) -> bool:
+    """Determine if the node has high concurrent ssh connections.
+
+    Args:
+        ip: The IP address to check
+        threshold: Maximum number of allowed concurrent SSH connections
+
+    Returns:
+        bool: True if number of concurrent SSH connections exceeds threshold
+    """
+    try:
+        # Use pgrep to efficiently find ssh processes and pipe to grep for IP
+        cmd = f'pgrep -f ssh | xargs -r ps -p | grep -c {ip}'
+        proc = subprocess.run(cmd,
+                              shell=True,
+                              stdout=subprocess.PIPE,
+                              stderr=subprocess.PIPE,
+                              text=True,
+                              check=False)
+        if proc.returncode == 0:
+            count = int(proc.stdout.strip())
+            return count >= _MAX_CONCURRENT_SSH_CONNECTIONS
+        return False
+    except (subprocess.SubprocessError, ValueError):
+        return False