Granny
Gaining Access
Nmap scan:

IIS 6.0
This machine is running an outdated version of Microsoft IIS, which is vulnerable to a RCE exploit.
Using this, we can gain a reverse shell easily:


Privilege Escalation
Churrasco
We can enumerate the machine using systeminfo.

This is a really old version of Windows that is outdated and vulnerable to loads of exploits. One exploit is the Churrasco exploit, which works on Windows Server 2003 machines. However, because this machine was so old, it was hard to transfer files over to it using conventional Windows methods.
So, we would need to create a wget binaruy using vbs.
Afterwards, we can download the binary from here:
The exploit works through impersonating the SYSTEM user to execute commands by stealing the tokens from the worker processes run by the SYSTEM user.
The exploit can be used to gain a reverse shell easily via nc.exe:

A listener port would have a shell as SYSTEM after execution.