diff --git a/dcos/mesos.py b/dcos/mesos.py
index c1923e7..06203ff 100644
--- a/dcos/mesos.py
+++ b/dcos/mesos.py
@@ -1053,6 +1053,12 @@ class TaskIO(object):
         self.attach_input_event = threading.Event()
         self.attach_input_event.clear()
 
+        # Set up an event to block printing the output
+        # until an attach input event has successfully
+        # been established.
+        self.print_output_event = threading.Event()
+        self.print_output_event.clear()
+
         # Set up an event to block the main thread
         # from exiting until signaled to do so.
         self.exit_event = threading.Event()
@@ -1233,6 +1239,12 @@ class TaskIO(object):
         # stream to be attached by setting an event.
         self.attach_input_event.set()
 
+        # If we are running in interactive mode, wait to make sure that
+        # our input connection succeeds before pushing any output to the
+        # output queue.
+        if self.interactive:
+            self.print_output_event.wait()
+
         try:
             for chunk in response.iter_content(chunk_size=None):
                 records = self.decoder.decode(chunk)
@@ -1251,12 +1263,13 @@ class TaskIO(object):
         """Streams all input data (e.g. STDIN) from the client to the agent
         """
 
-        def _input_streamer():
-            """Generator function yielding ATTACH_CONTAINER_INPUT
-            messages for streaming. It creates the initial
-            ATTACH_CONTAINER_INPUT message to establish the
-            connection, then yields a message from the input_queue on
-            each subsequent call.
+        def _initial_input_streamer():
+            """Generator function yielding the initial ATTACH_CONTAINER_INPUT
+            message for streaming. We have a separate generator for this so
+            that we can attempt the connection once before committing to a
+            persistent connection where we stream the rest of the input.
+
+            :returns: A RecordIO encoded message
             """
 
             message = {
@@ -1271,6 +1284,17 @@ class TaskIO(object):
 
             yield self.encoder.encode(message)
 
+        def _input_streamer():
+            """Generator function yielding ATTACH_CONTAINER_INPUT
+            messages for streaming. It yields the _intitial_input_streamer()
+            message, followed by messages from the input_queue on each
+            subsequent call.
+
+            :returns: A RecordIO encoded message
+            """
+
+            yield next(_initial_input_streamer())
+
             while True:
                 record = self.input_queue.get()
                 if not record:
@@ -1291,6 +1315,19 @@ class TaskIO(object):
         # `_process_output_stream` function signals us that it's ready.
         self.attach_input_event.wait()
 
+        # Send an intial "Test" message to ensure that we can establish a
+        # connection with the agent at all. If we can't we will throw an
+        # exception and break out of this thread.
+        http.post(
+            self.agent_url,
+            data=_initial_input_streamer(),
+            **req_extra_args)
+
+        # If we succeeded with that connection, unblock process_output_stream()
+        # from sending output data to the output thread.
+        self.print_output_event.set()
+
+        # Begin streaming the the input.
         http.post(
             self.agent_url,
             data=_input_streamer(),