Trumps probation officer gets to question Trump. And it's mandatory he answer, except for 5th amendment exceptions.
And it's standard for the officer to ask for a full list of drugs the parolee is taking, and the doctor who prescribed them.
In addition it's likely that a parolees medical records are either through voluntary waiver, or court order, reviewed.
www.criminaljustice.ny.gov
348.3 Supervision recordkeeping requirements.
(b) Mandatory Sharing of Case Record Information.
A probation director, or his/her designee, must make available a copy of its pre-plea/pre-sentence report
and any medical, psychiatric or social agency report submitted in connection with its pre-sentence investigation or its supervision of a defendant, to any court or to the probation department of any court within the state
In any such case, the state department receiving such material must retain it under the same conditions of confidentiality as apply to the probation department that made it available.
