This summer I built this study aid for myself and STEM students to generate math problems so I can drill the art of problem solving with pen and paper. I don't see why there couldn't be a linguistically-fluent and artificially intelligent agent that generates philosophical problems to users to solve by hand. The agent could generate its own solution so the student can compare answers.
Going off the Merriam-Webster definition of philosophy:
"a theory underlying or regarding a sphere of activity or thought"
Maybe a computer program could generate potential and relevant activities or thoughts. Then the user of the program can then write their own responsive theory underlying or regarding to the generated example of an activity or thought. The agent could also generate its own answer so the student can compare answers.