diff --git a/python/ray/autoscaler/commands.py b/python/ray/autoscaler/commands.py
index f0b836748..0961642ad 100644
--- a/python/ray/autoscaler/commands.py
+++ b/python/ray/autoscaler/commands.py
@@ -199,9 +199,16 @@ def get_or_create_head_node(config, config_file, no_restart, restart_only, yes,
                 config["cluster_name"])
             provider.create_node(config["head_node"], head_node_tags, 1)
 
-        nodes = provider.non_terminated_nodes(head_node_tags)
-        assert len(nodes) == 1, "Failed to create head node."
-        head_node = nodes[0]
+        start = time.time()
+        head_node = None
+        while True:
+            if time.time() - start > 5:
+                raise RuntimeError("Failed to create head node.")
+            nodes = provider.non_terminated_nodes(head_node_tags)
+            if len(nodes) == 1:
+                head_node = nodes[0]
+                break
+            time.sleep(1)
 
         # TODO(ekl) right now we always update the head node even if the hash
         # matches. We could prompt the user for what they want to do here.