diff --git a/lib/ansible/runner/connection_plugins/paramiko_ssh.py b/lib/ansible/runner/connection_plugins/paramiko_ssh.py
index 3ae76fe547..22f57a6afe 100644
--- a/lib/ansible/runner/connection_plugins/paramiko_ssh.py
+++ b/lib/ansible/runner/connection_plugins/paramiko_ssh.py
@@ -31,6 +31,7 @@ import random
 import logging
 import traceback
 import fcntl
+import re
 import sys
 from termios import tcflush, TCIFLUSH
 from binascii import hexlify
@@ -210,12 +211,17 @@ class Connection(object):
                 shcmd, prompt, success_key = utils.make_sudo_cmd(sudo_user, executable, cmd)
             elif self.runner.su or su:
                 shcmd, prompt, success_key = utils.make_su_cmd(su_user, executable, cmd)
+                prompt_re = re.compile(prompt)
             vvv("EXEC %s" % shcmd, host=self.host)
             sudo_output = ''
             try:
                 chan.exec_command(shcmd)
                 if self.runner.sudo_pass or self.runner.su_pass:
-                    while not sudo_output.endswith(prompt) and success_key not in sudo_output:
+                    while True:
+                        if success_key in sudo_output or \
+                            (self.runner.sudo_pass and sudo_output.endswith(prompt)) or \
+                            (self.runner.su_pass and prompt_re.match(sudo_output)):
+                            break
                         chunk = chan.recv(bufsize)
                         if not chunk:
                             if 'unknown user' in sudo_output:
diff --git a/lib/ansible/runner/connection_plugins/ssh.py b/lib/ansible/runner/connection_plugins/ssh.py
index 17895729e4..8a12356cd5 100644
--- a/lib/ansible/runner/connection_plugins/ssh.py
+++ b/lib/ansible/runner/connection_plugins/ssh.py
@@ -17,6 +17,7 @@
 #
 
 import os
+import re
 import subprocess
 import shlex
 import pipes
@@ -268,6 +269,7 @@ class Connection(object):
 
         if su and su_user:
             sudocmd, prompt, success_key = utils.make_su_cmd(su_user, executable, cmd)
+            prompt_re = re.compile(prompt)
             ssh_cmd.append(sudocmd)
         elif not self.runner.sudo or not sudoable:
             prompt = None
@@ -308,7 +310,12 @@ class Connection(object):
             sudo_output = ''
             sudo_errput = ''
 
-            while not sudo_output.endswith(prompt) and success_key not in sudo_output:
+            while True:
+                if success_key in sudo_output or \
+                    (self.runner.sudo_pass and sudo_output.endswith(prompt)) or \
+                    (self.runner.su_pass and prompt_re.match(sudo_output)):
+                    break
+
                 rfd, wfd, efd = select.select([p.stdout, p.stderr], [],
                                               [p.stdout], self.runner.timeout)
                 if p.stderr in rfd:
diff --git a/lib/ansible/utils/__init__.py b/lib/ansible/utils/__init__.py
index 3283b0bae2..1800a35534 100644
--- a/lib/ansible/utils/__init__.py
+++ b/lib/ansible/utils/__init__.py
@@ -950,9 +950,9 @@ def make_su_cmd(su_user, executable, cmd):
     """
     # TODO: work on this function
     randbits = ''.join(chr(random.randint(ord('a'), ord('z'))) for x in xrange(32))
-    prompt = 'assword: '
+    prompt = '[Pp]assword: ?$'
     success_key = 'SUDO-SUCCESS-%s' % randbits
-    sudocmd = '%s %s %s %s -c %s' % (
+    sudocmd = '%s %s %s -c "%s -c %s"' % (
         C.DEFAULT_SU_EXE, C.DEFAULT_SU_FLAGS, su_user, executable or '$SHELL',
         pipes.quote('echo %s; %s' % (success_key, cmd))
     )
diff --git a/test/units/TestUtils.py b/test/units/TestUtils.py
index c60a0d8291..6241fd7798 100644
--- a/test/units/TestUtils.py
+++ b/test/units/TestUtils.py
@@ -3,6 +3,7 @@
 import unittest
 import os
 import os.path
+import re
 import tempfile
 import yaml
 import passlib.hash
@@ -511,8 +512,8 @@ class TestUtils(unittest.TestCase):
         cmd = ansible.utils.make_su_cmd('root', '/bin/sh', '/bin/ls')
         self.assertTrue(isinstance(cmd, tuple))
         self.assertEqual(len(cmd), 3)
-        self.assertTrue(' root /bin/sh' in cmd[0])
-        self.assertTrue(cmd[1] == 'assword: ')
+        self.assertTrue(' root -c "/bin/sh' in cmd[0])
+        self.assertTrue(re.compile(cmd[1]))
         self.assertTrue('echo SUDO-SUCCESS-' in cmd[0] and cmd[2].startswith('SUDO-SUCCESS-'))
 
     def test_to_unicode(self):