I think it's normal unfortunately for people with ADD to have trouble with starting & completing tasks. I have it, my 18 & 19 year olds have it. Looking back I wish I would've helped them more. I was worn out by the time they were 15, but now that age seems so young. Neither completed high school & I wish I would've helped them find more success.

If he doesn't respond to the negative consequences, like most with disorders it seems have that trait. It's like life is hard enough as it is, may as well get used to failing.

Focus on the small successes, send the message that you believe in him that he can do it. School days are likely stressful for him, I don't know how understanding the staff is or other peers. Kids & teachers can wreak havoc on self esteem.

It's a delicate age, a lot at risk like his self-esteem, risk of falling into a bad crowd that's given up trying to achieve. Both my older kids have drug issues, I'm glad you don't have that with him, but it's another risk to kids with disorders, or even any kid that age.

you don't have to bail him out of the service hours, but I think you should help him with it. Those hours can usually be done at home, our schools always allowed it. Helping around the house, helping with younger sister, etc. Why not help him have some successes like that, the small stuff that could help put some wind under his sails. You're not doing it for him, just shining a light on the path. show him you're proud of him for those things he does, like being a good kid, having a big heart, being a good big brother. Let him know these challenges are something you will get through together. you could even let him know it's hard for you to arrange & remind all the assignments, and it would be so appreciated & helpful if he could write down his assignments each day & get the homework done & out of the way. And that you adore him & believe he can do this.

I was worried about babying them, wanted them to learn how to adapt & realize they may have to work harder than the kids who easily remember their assignments & easily mold into the expected behavior. And I was offended when a counselor told me kindly she felt I needed to baby my son a little more. But in hindsight I feel she was right. The outside world is cruel enough.