diff --git a/python/ray/autoscaler/command_runner.py b/python/ray/autoscaler/command_runner.py
index 6a10654ea..4b38108eb 100644
--- a/python/ray/autoscaler/command_runner.py
+++ b/python/ray/autoscaler/command_runner.py
@@ -220,7 +220,8 @@ class SSHOptions:
         self.arg_dict["ConnectTimeout"] = "{}s".format(timeout)
         return ["-i", self.ssh_key] + [
             x for y in (["-o", "{}={}".format(k, v)]
-                        for k, v in self.arg_dict.items()) for x in y
+                        for k, v in self.arg_dict.items()
+                        if v is not None) for x in y
         ]
 
 
@@ -243,8 +244,11 @@ class SSHCommandRunner(CommandRunnerInterface):
         self.ssh_user = auth_config["ssh_user"]
         self.ssh_control_path = ssh_control_path
         self.ssh_ip = None
-        self.base_ssh_options = SSHOptions(self.ssh_private_key,
-                                           self.ssh_control_path)
+        self.ssh_proxy_command = auth_config.get("ssh_proxy_command", None)
+        self.ssh_options = SSHOptions(
+            self.ssh_private_key,
+            self.ssh_control_path,
+            ProxyCommand=self.ssh_proxy_command)
 
     def _get_node_ip(self):
         if self.use_internal_ip:
@@ -292,7 +296,7 @@ class SSHCommandRunner(CommandRunnerInterface):
             with_output=False,
             ssh_options_override=None,
             **kwargs):
-        ssh_options = ssh_options_override or self.base_ssh_options
+        ssh_options = ssh_options_override or self.ssh_options
 
         assert isinstance(
             ssh_options, SSHOptions
@@ -342,8 +346,8 @@ class SSHCommandRunner(CommandRunnerInterface):
         self._set_ssh_ip_if_required()
         self.process_runner.check_call([
             "rsync", "--rsh",
-            " ".join(["ssh"] +
-                     self.base_ssh_options.to_ssh_options_list(timeout=120)),
+            subprocess.list2cmdline(
+                ["ssh"] + self.ssh_options.to_ssh_options_list(timeout=120)),
             "-avz", source, "{}@{}:{}".format(self.ssh_user, self.ssh_ip,
                                               target)
         ])
@@ -352,8 +356,8 @@ class SSHCommandRunner(CommandRunnerInterface):
         self._set_ssh_ip_if_required()
         self.process_runner.check_call([
             "rsync", "--rsh",
-            " ".join(["ssh"] +
-                     self.base_ssh_options.to_ssh_options_list(timeout=120)),
+            subprocess.list2cmdline(
+                ["ssh"] + self.ssh_options.to_ssh_options_list(timeout=120)),
             "-avz", "{}@{}:{}".format(self.ssh_user, self.ssh_ip,
                                       source), target
         ])
diff --git a/python/ray/autoscaler/commands.py b/python/ray/autoscaler/commands.py
index a60f5a9bb..1840dcdc6 100644
--- a/python/ray/autoscaler/commands.py
+++ b/python/ray/autoscaler/commands.py
@@ -321,6 +321,9 @@ def get_or_create_head_node(config, config_file, no_restart, restart_only, yes,
 
         # Rewrite the auth config so that the head node can update the workers
         remote_config = copy.deepcopy(config)
+        # drop proxy options if they exist, otherwise
+        # head node won't be able to connect to workers
+        remote_config["auth"].pop("ssh_proxy_command", None)
         if config["provider"]["type"] != "kubernetes":
             remote_key_path = "~/ray_bootstrap_key.pem"
             remote_config["auth"]["ssh_private_key"] = remote_key_path
diff --git a/python/ray/autoscaler/ray-schema.json b/python/ray/autoscaler/ray-schema.json
index ad299ebf5..2c3fead8e 100644
--- a/python/ray/autoscaler/ray-schema.json
+++ b/python/ray/autoscaler/ray-schema.json
@@ -173,6 +173,10 @@
                 },
                 "ssh_private_key": { 
                     "type": "string"
+                },
+                "ssh_proxy_command": {
+                    "description": "A value for ProxyCommand ssh option, for connecting through proxies. Example: nc -x proxy.example.com:1234 %h %p",
+                    "type": "string"
                 }
             }
         },