Retired - Legacy

I am taking my time to go through different boxes in preparation for my OSCP. I am documenting Legacy now. I understand the exploits to be used but I am having an issue that I don’t quite understand.

All of this is without MSF. All by hand.

When I send the exploit that I created via msvenom, I do get a return shell attempt. Instead of getting windows prompt, I get nothing more than a flashing cursor. If I type anything and hit enter, it will crash the shell.

I reset the box, tried from multiple images of kali, and performed this across several days.

I am sure it is something on my side and was hoping someone could shed some light on why this is happening.

I can list the steps and exploits I am using, if that is allowed.

At a guess, and this is just a guess without knowing any specifics, I’d start by checking the payload matches the listener.

The most common issue here is staged payloads hitting a listener that cant send the second stage (such as netcat), but that might not explain why its just a flashing cursor.

This is a retired box, so you can pretty much put whatever you want, there are full walkthroughs if people want spoilers.