I was working during high school for a non-profit in the 90s. They had machines that were on the end of life-cycle. One had a hard disk that was making huge noise similar to circular saw. I knew from experience that this sound probably comes from the resonation of the mechanical metal disk on top of the hard disk, and it can be solved by pushing the disk in just slightly. And it worked.
Another one was during high school as well, as an exchange student. In the computer science class there was a certain network game, and we were joking about high scores. So I checked out the score file format using hex editor, and created a tool that was able to modify the high score table.
When in the university, I needed to graduate soon, as I was heading to Silicon Valley. I had one weekend reserved to do a major statistics assignment. The assignment had to be done using a certain MS-DOS based tool, created by the professor. I had planned to use university computers to do it, but my electronic key had expired. It was not possible to extend the key during the weekend. It was possible to get a license for your own laptop, but even that required somebody to give you the licensing key, and that was not possible during the weekend. So I started my assignment by cracking the licensing for the tool. The licensing was based on a challenge, that was based on random number. Fortunately for me, the random number seed was the time (in seconds). So I put the machine to work for the first night, and it was able to brute-force the right challenge by resetting the system clock before each trial.
Later years one hack that I was proud about was creating an entry in the Linux drivers for my digital camera, and I submitted it as a patch as well.
Not a Windows guy, but I was working on a server software that was also ported to Windows. We had a weird timing bug that we knew approximately how to reproduce, but it was so rare we could not do it, and it was happening only with production version, not debug version, and only on Windows. We did not have a core dump (or whatever that was called on Windows at the time). So I created a framework to start the server, execute the operation on the server, and use Windows facilities catch crashes and save the core dump. With that framework I was able to find and fix the bug.
My latest proud hack is a system for time lapse microscopic photography. I have a lab microscope, and I mounted a Canon DSLR on top of it. An Arduino is connected to the camera through remote shutter port, so I can wake up the camera from sleep. I had to create the shutter control hardware on the Arduino from a remote shutter button. The Arduino is also controlling a stepper motor, which has a Lego wheel on, which on turn has a caterpillar track, which in turn is controlling the zoom on the microscope. This allows me to control the Arduino zoom. Then I have created custom keep-focus software, which uses images from the DSLR, and calculates how close the image is to the original, and tries various adjustments to find where the focus is closest.