Tryhackme writeup: Retro

Boot to root: Retro wordpress theme & exploitation of CVE-2019-1388

Initial recon + Access:

Results from nmap (Filtering was enabled. The option -Pn was necessary in this box):

80/tcp   open  http
3389/tcp open  ms-wbt-server

IIS Server running @ port 80

We can run a directory scan with gobuster, but we can first try “retro” as the directory.



Navigating within the page, we see a login page at /retro/wp-login.php

User: Wade, password unknown yet. Admin user was invalid at …/wp-login.php, so we guess “wade” can be an administrator of the site.


There is one blog post called “Ready player one”, in which there is a comment from Wade himself, about trying not to forget his favourite character “parzival” and so on.

We try logging in with <wade:parzival>, and we’re into the wordpress administration page! We could try to exploit wordpress themes by uploading a custom php reverse shell, but seeing there is an rdp service running, we can try to connect with xfreerdp and this credentials.


And we’re in!


Opening Google chrome (I was expecting to see some information on History/passwords/etc.), there is a bookmark for NIST referencing CVE-2019-1388, which is itself a clue (maybe), about a vulnerability issuing “Windows Certificate Dialog Elevation of Privilege Vulnerability”.

CVE 2019-1388

(NIST) CVE-2019-1388

This points to an issue with the UAC in Windows:

Whenever we run a verified executable (This can’t be done with unsigned .exe) as administrator, and we’re prompted for the admin password, we can click the link of the path to the certificate, and this will open a browser as administrator, since we’re still on the UAC.

Then, we can save the browser’s page (save as), and at the saving window, instead of actually saving the html, we navigate to C:/users/user/windows/system32/ and open cmd.exe.

PoC video:

Remember, we’re still under the UAC process, so whatever we do here, will be executed as administrator:


This way we secured the flag by just reading it from the cmd (Or opening > notepad root.txt.txt because the selection and copy/paste functions directly at the terminal were not available).

Written By


Cybersecurity professional and IT enthusiast with a passion for technology, music, personal growth, and Eastern philosophy. Transitioned from mechanical engineering to IT in 2020, with a full-time interest in Technology, Cybersecurity and recent advances in AI. Seeks to integrate eastern philosophy, mindfulness and a growth mindset into daily life and work.