PeekABoo : Penetration Testing To Enable Remote Desktop On The Targeted Machine

PeekABoo tool can be used during internal penetration testing when a user needs to enable Remote Desktop on the targeted machine. It uses PowerShell remoting to perform this task.

The tool only works if WinRM is enabled. Since Windows Server 2012 WinRM is enabled by default on all Windows server operating systems, but not on client operating systems.

Note: Remote desktop is disabled by default on all Windows operating systems. User would require local administrator password or administrator privileges on the server to enable RDP on a targeted machine.

Also Read – Joy : To Capture & Analyse Network Flow Data & Intraflow Data


Targeted machine on an internal network has RDP disabled:

Enabling remote desktop service on a targeted machine by pressing option 2:

Successfully enabled remote desktop service on a targeted machine:

How to install?

– git clone
– cd PeekABoo
– python

How do I use this?

  • Press 1: This will set the PowerShell to unrestricted mode.
  • Press 2: It enables the Remote Desktop on the targeted machine and shows the RDP port (3389) status.
  • Press 3: It disables the Remote Desktop on the targeted machine.
  • Press 4: To exit from the program.

My Windows machine do not have Python installed, what should I do?

  • Download an exe from the release section of the Github along with PowerShell files available here or do it on your own using PyInstaller after reviewing the source code.
  • Compile into an executable using Pyinstaller
  • PyInstaller is available on PyPI. You can install it through pip:

pip install pyinstaller