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If I try to parse this:
1. **Introduction to Legal Principles**
1) Historical Context
2) Core Doctrines
i. Doctrine of Precedent
ii. Doctrine of Equity
3) Sources of Law
2. **Civil Procedure**
A) Pleadings and Motions
a. The Complaint
b. The Answer
c. Pre-trial Motions
B) Discovery Process
C) Trial Proceedings
I get the proper AST:

However, if I change the list before the roman numerals in lowercase to a list with roman numbers in uppercase like this:
1. **Introduction to Legal Principles**
I) Historical Context
II) Core Doctrines
i. Doctrine of Precedent
ii. Doctrine of Equity
III) Sources of Law
2. **Civil Procedure**
A) Pleadings and Motions
a. The Complaint
b. The Answer
c. Pre-trial Motions
B) Discovery Process
C) Trial Proceedings
the AST generated is wrong, as it didn't create a third level for the list with lowercase roman numerals:
