I am 72 and retired, and have an 81-year-old husband who has health challenges. My youngest child, now 33, was recently incarcerated for the third time. I have four older children who are all thriving — one, ironically, works for a nonprofit law center seeking to reform the criminal-(in)justice system. My incarcerated son is an addict, has lied to me consistently since childhood and offended against a family member as a teenager. During a previous incarceration, he gave my phone number to a fellow inmate, who tried to extort money from me through his wife.

He just sent me a letter requesting that I provide him with commissary money, that I obtain and pay for a lawyer to represent him in his current parole-violation case, that I pay his court fines and that I send him “care packages.” A small special-needs trust fund for my son established by my late father has a balance of about $20,000 after previous withdrawals for similar requests. As trustee, I have the ability to grant his requests, but I’m not inclined to do so, based on past experiences. After his second incarceration, he was out of prison for only 10 days before reoffending. What is my ethical responsibility to my son, whom I adopted when he was 6, who is Black (I am not), but whose life has shown no improvement from Day 1 despite my considerable best efforts over many years? — Name Withheld

It’s always hard when a child gets into serious trouble. You’ve got responsibilities to him, because his welfare is a special concern of yours. At the same time, he has responsibilities to you, and clearly he has not met them. Of the things he’s asking for, legal representation seems the most important. A privately retained criminal attorney, paid for out of that dwindling trust fund, will probably be able to devote more time and resources to his case than a public defender could. Commissary money can go toward what most people consider basic necessities (soap, shampoo, toilet paper). And you’d be lifting one of the barriers to his reintegration after he leaves prison if you allowed the trust fund to pay for the court fines.

Care packages, however, seem more appropriate in a relationship that’s in better shape than yours now is with him. Especially given your son’s history of addiction and self-sabotaging behavior, it’s important to set clear boundaries. You mentioned that his was a transracial adoption, as are perhaps 30 percent of domestic adoptions in the U.S., and perhaps you did so because you wonder whether that circumstance made his integration into your family more difficult or his sense of identity less secure. This is a complex topic, but the preponderance of the research hasn’t found an especially high rate of emotional or behavioral problems among transracial adoptees. And of course, this child has long been an adult. You want to give your son opportunities to live a better life, but enabling deceit and misconduct helps neither of you. If he continues to fail you and himself, you may have to part ways.