A circumstance is problematic when it is an obstacle to a goal and it is unclear how the obstacle is to be dealt with, as no clear solution is presenting itself. That which is problematic presents a "gnarly" problem, aka a "challenge".
So the Head of the Secret Intelligence Service could say of a job applicant for an Intelligence Analyst position, "His ears are problematic", if the applicant is the deaf nephew of the Prime Minister, and the duties of an analyst normally include listening in on wiretapped conversations. The situation the Head finds themselves in is "problematic" and "his ears" are an emblem for the entire situation.
Among the synonyms Merriam-Webster offers for problematic we find:
complex
tricky
thorny
sensitive
delicate
touchy
knotty