diff --git a/mitogen/ssh.py b/mitogen/ssh.py
index ee97425b..1a545964 100644
--- a/mitogen/ssh.py
+++ b/mitogen/ssh.py
@@ -31,6 +31,7 @@ Functionality to allow establishing new slave contexts over an SSH connection.
 """
 
 import logging
+import re
 import time
 
 try:
@@ -46,10 +47,16 @@ LOG = logging.getLogger('mitogen')
 
 # sshpass uses 'assword' because it doesn't lowercase the input.
 PASSWORD_PROMPT = b('password')
-PERMDENIED_PROMPT = b('permission denied')
 HOSTKEY_REQ_PROMPT = b('are you sure you want to continue connecting (yes/no)?')
 HOSTKEY_FAIL = b('host key verification failed.')
 
+# [user@host: ] permission denied
+PERMDENIED_RE = re.compile(
+    ('(?:[^@]+@[^:]+: )?'  # Absent in OpenSSH <7.5
+     'Permission denied').encode(),
+    re.I
+)
+
 
 DEBUG_PREFIXES = (b('debug1:'), b('debug2:'), b('debug3:'))
 
@@ -289,11 +296,7 @@ class Stream(mitogen.parent.Stream):
                 self._host_key_prompt()
             elif HOSTKEY_FAIL in buf.lower():
                 raise HostKeyError(self.hostkey_failed_msg)
-            elif buf.lower().startswith((
-                    PERMDENIED_PROMPT,
-                    b("%s@%s: " % (self.username, self.hostname))
-                        + PERMDENIED_PROMPT,
-                )):
+            elif PERMDENIED_RE.match(buf):
                 # issue #271: work around conflict with user shell reporting
                 # 'permission denied' e.g. during chdir($HOME) by only matching
                 # it at the start of the line.
diff --git a/tests/data/stubs/ssh.py b/tests/data/stubs/ssh.py
index 8df5aa39..63397479 100755
--- a/tests/data/stubs/ssh.py
+++ b/tests/data/stubs/ssh.py
@@ -15,6 +15,10 @@ Are you sure you want to continue connecting (yes/no)?
 
 HOST_KEY_STRICT_MSG = """Host key verification failed.\n"""
 
+PERMDENIED_CLASSIC_MSG = 'Permission denied (publickey,password)\n'
+PERMDENIED_75_MSG = 'chicken@nandos.com: permission denied (publickey,password)\n'
+
+
 
 def tty(msg):
     fp = open('/dev/tty', 'wb', 0)
@@ -37,13 +41,23 @@ def confirm(msg):
         fp.close()
 
 
-if os.getenv('FAKESSH_MODE') == 'ask':
+mode = os.getenv('FAKESSH_MODE')
+
+if mode == 'ask':
     assert 'y\n' == confirm(HOST_KEY_ASK_MSG)
 
-if os.getenv('FAKESSH_MODE') == 'strict':
+elif mode == 'strict':
     stderr(HOST_KEY_STRICT_MSG)
     sys.exit(255)
 
+elif mode == 'permdenied_classic':
+    stderr(PERMDENIED_CLASSIC_MSG)
+    sys.exit(255)
+
+elif mode == 'permdenied_75':
+    stderr(PERMDENIED_75_MSG)
+    sys.exit(255)
+
 
 #
 # Set an env var if stderr was a TTY to make ssh_test tests easier to write.
diff --git a/tests/ssh_test.py b/tests/ssh_test.py
index 179b543d..ca614fa2 100644
--- a/tests/ssh_test.py
+++ b/tests/ssh_test.py
@@ -124,9 +124,10 @@ class BannerTest(testlib.DockerMixin, unittest2.TestCase):
         self.assertEquals(name, context.name)
 
 
-class RequirePtyTest(testlib.DockerMixin, testlib.TestCase):
-    stream_class = mitogen.ssh.Stream
-
+class FakeSshMixin(testlib.RouterMixin):
+    """
+    Mix-in that provides :meth:`fake_ssh` executing the stub 'ssh.py'.
+    """
     def fake_ssh(self, FAKESSH_MODE=None, **kwargs):
         os.environ['FAKESSH_MODE'] = str(FAKESSH_MODE)
         try:
@@ -139,6 +140,20 @@ class RequirePtyTest(testlib.DockerMixin, testlib.TestCase):
         finally:
             del os.environ['FAKESSH_MODE']
 
+
+class PermissionDeniedTest(FakeSshMixin, testlib.TestCase):
+    def test_classic_prompt(self):
+        self.assertRaises(mitogen.ssh.PasswordError,
+            lambda: self.fake_ssh(FAKESSH_MODE='permdenied_classic'))
+
+    def test_openssh_75_prompt(self):
+        self.assertRaises(mitogen.ssh.PasswordError,
+            lambda: self.fake_ssh(FAKESSH_MODE='permdenied_75'))
+
+
+class RequirePtyTest(FakeSshMixin, testlib.TestCase):
+    stream_class = mitogen.ssh.Stream
+
     def test_check_host_keys_accept(self):
         # required=true, host_key_checking=accept
         context = self.fake_ssh(FAKESSH_MODE='ask', check_host_keys='accept')