diff --git a/pssh/ssh_client.py b/pssh/ssh_client.py
index c6e04f33..ffdeb773 100644
--- a/pssh/ssh_client.py
+++ b/pssh/ssh_client.py
@@ -290,8 +290,9 @@ def _mkdir(self, sftp, directory):
         try:
             sftp.mkdir(directory)
         except IOError, error:
-            logger.error("Error occured creating directory %s on %s - %s",
-                         directory, self.host, error)
+            msg = "Error occured creating directory %s on %s - %s"
+            logger.error(msg, directory, self.host, error)
+            raise IOError(msg, directory, self.host, error)
         logger.debug("Creating remote directory %s", directory)
         return True
 
@@ -372,6 +373,6 @@ def copy_file(self, local_file, remote_file, recurse=False):
         except Exception, error:
             logger.error("Error occured copying file %s to remote destination %s:%s - %s",
                          local_file, self.host, remote_file, error)
-        else:
-            logger.info("Copied local file %s to remote destination %s:%s",
-                        local_file, self.host, remote_file)
+            raise error
+        logger.info("Copied local file %s to remote destination %s:%s",
+                    local_file, self.host, remote_file)
diff --git a/requirements.txt b/requirements.txt
index 7420037d..afc628bb 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,2 +1,4 @@
+setuptools>=21.0
 paramiko>=1.12,!=1.16.0
-gevent>=1.1rc3
+gevent<=1.1; python_version < '3'
+gevent>=1.1; python_version >= '3'
diff --git a/setup.py b/setup.py
index 451920fd..b434f16e 100644
--- a/setup.py
+++ b/setup.py
@@ -29,6 +29,9 @@
       packages=find_packages('.', exclude=(
           'embedded_server', 'embedded_server.*')),
       install_requires=['paramiko', 'gevent'],
+      extras_require={':python_version < "3"': ['gevent<=1.1'],
+                      ':python_version >= "3"': ['gevent>=1.1'],
+                      },
       classifiers=[
         'License :: OSI Approved :: GNU Lesser General Public License v2 (LGPLv2)',
         'Intended Audience :: Developers',
diff --git a/tests/test_pssh_client.py b/tests/test_pssh_client.py
index 49894291..63fa8b8d 100644
--- a/tests/test_pssh_client.py
+++ b/tests/test_pssh_client.py
@@ -33,6 +33,8 @@
 import os
 import warnings
 import shutil
+import sys
+
 
 PKEY_FILENAME = os.path.sep.join([os.path.dirname(__file__), 'test_client_private_key'])
 USER_KEY = paramiko.RSAKey.from_private_key_file(PKEY_FILENAME)
@@ -390,6 +392,60 @@ def test_pssh_client_directory(self):
             self.assertTrue(os.path.isfile(path))
         shutil.rmtree(local_test_path)
         shutil.rmtree(remote_test_path)
+
+    def test_pssh_client_copy_file_failure(self):
+        """Test failure scenarios of file copy"""
+        test_file_data = 'test'
+        local_test_path = 'directory_test'
+        remote_test_path = 'directory_test_copied'
+        for path in [local_test_path, remote_test_path]:
+            mask = int('0700') if sys.version_info <= (2,) else 0o700
+            if os.path.isdir(path):
+                os.chmod(path, mask)
+            for root, dirs, files in os.walk(path):
+                os.chmod(root, mask)
+                for _path in files + dirs:
+                    os.chmod(os.path.join(root, _path), mask)
+            try:
+                shutil.rmtree(path)
+            except OSError:
+                pass
+        os.mkdir(local_test_path)
+        os.mkdir(remote_test_path)
+        local_file_path = os.path.join(local_test_path, 'test_file')
+        remote_file_path = os.path.join(remote_test_path, 'test_file')
+        test_file = open(local_file_path, 'w')
+        test_file.write('testing\n')
+        test_file.close()
+        # Permission errors on writing into dir
+        mask = 0111 if sys.version_info <= (2,) else 0o111
+        os.chmod(remote_test_path, mask)
+        client = ParallelSSHClient([self.host], port=self.listen_port,
+                                   pkey=self.user_key)
+        cmds = client.copy_file(local_test_path, remote_test_path, recurse=True)
+        for cmd in cmds:
+            try:
+                cmd.get()
+                raise Exception("Expected IOError exception, got none")
+            except IOError:
+                pass
+        self.assertFalse(os.path.isfile(remote_file_path))
+        # Create directory tree failure test
+        local_file_path = os.path.join(local_test_path, 'test_file')
+        remote_file_path = os.path.join(remote_test_path, 'test_dir', 'test_file')
+        cmds = client.copy_file(local_file_path, remote_file_path, recurse=True)
+        for cmd in cmds:
+            try:
+                cmd.get()
+                raise Exception("Expected IOError exception on creating remote "
+                                "directory, got none")
+            except IOError:
+                pass
+        self.assertFalse(os.path.isfile(remote_file_path))
+        mask = int('0600') if sys.version_info <= (2,) else 0o600
+        os.chmod(remote_test_path, mask)
+        for path in [local_test_path, remote_test_path]:
+            shutil.rmtree(path)
     
     def test_pssh_pool_size(self):
         """Test setting pool size to non default values"""