What are my chances of re-enlisting with a waiver for a personality disorder?

I can look at our medical waivers and give you an answer, I work at the largest Army recruiting BN. If you want to send me your documents I can read them and give you my best guess, but a lot of what the above comments stated are true.

Go see a Recruiter and ask.

But be aware you will be denied to even try to process if you're taking medication, and if you've been off, you will need records of -everything- you've ever taken as well as a note from the prescribing doctor saying you've been off of it for years-- and even then, it probably won't be approved. For perspective, people aren't even being approved for ADD in high school after years in college.

Extremely unlikely. However, every waiver is done by the DA Surgeon. Submit your documents and say a prayer. If you want an honest opinion , it's most likely going to be disapproved.