I found a method where you create a .bat and archive it using winrar. Doing so will allow you to call a picture/document and have the desired bar run in the background (after extraction).
Sauce: [How to hide a Bat file inside an image](https://youtu.be/ytvKVYYrqEw)
I am not incredibly experienced in PenTesting (working towards it). Maybe it will be of some use. 🙂