Endpoint Security case study

Controlled Windows Exploitation and Reverse Shell Lab

Completed a controlled four-stage Windows exploitation exercise using a tunnel, a generated reverse TCP payload, a Metasploit handler, and a verified remote shell.

Skills demonstrated

  • Exposed the local Metasploit listener through ngrok.
  • Generated a Windows executable reverse TCP payload with the tunnel callback settings.
  • Delivered and executed the payload on an authorized remote VM.
  • Started multi/handler and confirmed a remote session.

Tools used

  • Metasploit
  • msfvenom
  • Meterpreter
  • multi/handler
  • ngrok
  • Windows VM

Technical walkthrough

Lab evidence and investigation steps.

Open on GitHub
Ref 1: Ngrok setup and listening on port 4444
Ref 1: Ngrok setup and listening on port 4444
Ref 2: Meterpreter reverse tcp payload setup to direct traffic to ngrok on port 19504. Payload is exe format so that its executed on windows
Ref 2: Meterpreter reverse tcp payload setup to direct traffic to ngrok on port 19504. Payload is exe format so that its executed on windows
Ref 3: Payload delivered on windows computer and executed
Ref 3: Payload delivered on windows computer and executed
Ref 4: Metasploit handler listening on localhost port 4444
Ref 4: Metasploit handler listening on localhost port 4444
Ref 5: Shell attained on remote windows computer
Ref 5: Shell attained on remote windows computer