Brenda recently drove 12 hours to bail her 29-year-old son Tyler out of jail for the thirteenth time. After picking up Tyler, who has been arrested 14 times and through drug treatment nine times, Brenda took him for his favorite meal of ice cream and sushi.

"I totally feel like I failed as a parent," Brenda says, explaining that Tyler is addicted to heroin, and claiming that she, her husband and Tyler’s biological father have spent a combined $100,000 in the last decade bailing him out, getting him treatment, and paying for his expenses.

“I am 100 percent obsessed with fixing Tyler," adds Brenda, whom friends and family call "the ultimate enabler."

WATCH: A Stern Wake-Up Call for Mother Who Admits to Enabling Son’s Drug Use

Tyler recognizes that his upbringing and his mom's willingness to continually provide for him have been problematic. "The house was immaculate, the beds were always made, the laundry done, we looked good, and honestly it messed me up a little bit," he says about his childhood. "It crippled me in a way because I felt like I didn't have to work for anything. I had no responsibilities. Once I started using drugs, I felt like everything was still going to be provided for me and I didn't have to work for it."

WATCH: Drug User Admits Stealing From Family, Friends To Support His $100K Habit

Watch the video above as they turn to Dr. Phil for help.

"Do you believe in this rule that is real fundamental to me: You just simply do not reward bad behavior. Can we agree on that?"

Brenda responds, "When he gets out [of jail], where's he going to go? He can't go on the streets because then he'll just go back to drugs again."

Dr. Phil fires back: "Hell no he's not going to be on the street - he's going to go eat sushi and ice cream!"

How can Tyler turn his life around, and what should Brenda's role be so she doesn't further cripple her son? Watch more from this show.