diff --git a/docker/types/daemon.py b/docker/types/daemon.py
index ee8624e8..700f9a90 100644
--- a/docker/types/daemon.py
+++ b/docker/types/daemon.py
@@ -5,6 +5,8 @@ try:
 except ImportError:
     import urllib3
 
+from ..errors import DockerException
+
 
 class CancellableStream(object):
     """
@@ -55,9 +57,17 @@ class CancellableStream(object):
                 elif hasattr(sock_raw, '_sock'):
                     sock = sock_raw._sock
 
+            elif hasattr(sock_fp, 'channel'):
+                # We're working with a paramiko (SSH) channel, which doesn't
+                # support cancelable streams with the current implementation
+                raise DockerException(
+                    'Cancellable streams not supported for the SSH protocol'
+                )
             else:
                 sock = sock_fp._sock
-            if isinstance(sock, urllib3.contrib.pyopenssl.WrappedSocket):
+
+            if hasattr(urllib3.contrib, 'pyopenssl') and isinstance(
+                    sock, urllib3.contrib.pyopenssl.WrappedSocket):
                 sock = sock.socket
 
             sock.shutdown(socket.SHUT_RDWR)
diff --git a/tests/integration/api_container_test.py b/tests/integration/api_container_test.py
index 249ef7cf..02f36033 100644
--- a/tests/integration/api_container_test.py
+++ b/tests/integration/api_container_test.py
@@ -883,6 +883,8 @@ Line2'''
         assert logs == (snippet + '\n').encode(encoding='ascii')
 
     @pytest.mark.timeout(5)
+    @pytest.mark.skipif(os.environ.get('DOCKER_HOST', '').startswith('ssh://'),
+                        reason='No cancellable streams over SSH')
     def test_logs_streaming_and_follow_and_cancel(self):
         snippet = 'Flowering Nights (Sakuya Iyazoi)'
         container = self.client.create_container(
@@ -1255,7 +1257,8 @@ class AttachContainerTest(BaseAPIIntegrationTest):
         assert output == 'hello\n'.encode(encoding='ascii')
 
     @pytest.mark.timeout(5)
-    @pytest.mark.xfail(True, reason='Cancellable events broken over SSH')
+    @pytest.mark.skipif(os.environ.get('DOCKER_HOST', '').startswith('ssh://'),
+                        reason='No cancellable streams over SSH')
     def test_attach_stream_and_cancel(self):
         container = self.client.create_container(
             BUSYBOX, 'sh -c "echo hello && sleep 60"',
diff --git a/tests/integration/models_containers_test.py b/tests/integration/models_containers_test.py
index ab41ea57..b48f6fb6 100644
--- a/tests/integration/models_containers_test.py
+++ b/tests/integration/models_containers_test.py
@@ -1,3 +1,4 @@
+import os
 import tempfile
 import threading
 
@@ -146,6 +147,8 @@ class ContainerCollectionTest(BaseIntegrationTest):
         assert logs[1] == b'world\n'
 
     @pytest.mark.timeout(5)
+    @pytest.mark.skipif(os.environ.get('DOCKER_HOST', '').startswith('ssh://'),
+                        reason='No cancellable streams over SSH')
     def test_run_with_streamed_logs_and_cancel(self):
         client = docker.from_env(version=TEST_API_VERSION)
         out = client.containers.run(