What is “outline server”? This https://getoutline.org/ ?
The main problem with trying to hack anything into the first gen My Cloud OS is the custom nature of the OS itself. It is not standard Linux, rather one has to build the package for it. Primarily the problem is, if I remember right, due to the non standard page size WD used in the first gen firmware.
Instead one may have to install a custom OS firmware, various discussions on various alternate OS’s in the following link, and then try to install what ever the server is that you are asking about.
