Nested lists of roman numerals that differ in casing fail to parse properly #747

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claunia · 2026-01-29T14:44:41Z

claunia commented

2026-01-29 14:44:41 +00:00

Originally created by @manutiedra on GitHub (Jul 19, 2025).

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:

Originally created by @manutiedra on GitHub (Jul 19, 2025). 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: <img width="670" height="827" alt="Image" src="https://github.com/user-attachments/assets/6cdc2816-ea51-4234-a8c0-fbc61898f1f1" /> 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: <img width="607" height="842" alt="Image" src="https://github.com/user-attachments/assets/87f1180d-6bf6-4271-b5ff-0d50d6081a66" />

claunia added the question label 2026-01-29 14:44:41 +00:00

claunia commented

2026-01-29 14:44:43 +00:00

@grc4kd commented on GitHub (Oct 4, 2025):

Hi, I was able to reproduce and dig into the issue a little bit, and I may have a solution.

Adding spaces for indentation before the third-level nested list element appears to resolve the issue. Specifically, I tried adding one extra space to the nested list items opening:

II) Core Doctrines
   i. Doctrine of Precedent
   ii. Doctrine of Equity

to:

II) Core Doctrines
  ->i. Doctrine of Precedent
  ->ii. Doctrine of Equity

Resulting in the following markdown input:

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

From what I can gather, the normal indentation rules about nested lists are causing the issue, where there was not enough indentation away from the list item delimiter ) in the line II) Core Doctrines.

Does this help explain the unexpected behavior?

@grc4kd commented on GitHub (Oct 4, 2025): Hi, I was able to reproduce and dig into the issue a little bit, and I may have a solution. Adding spaces for indentation before the third-level nested list element appears to resolve the issue. Specifically, I tried adding one extra space to the nested list items opening: ``` II) Core Doctrines i. Doctrine of Precedent ii. Doctrine of Equity ``` to: ``` II) Core Doctrines ->i. Doctrine of Precedent ->ii. Doctrine of Equity ``` Resulting in the following markdown input: ```markdown 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 ``` From what I can gather, the normal indentation rules about nested lists are causing the issue, where there was not enough indentation away from the list item delimiter `)` in the line `II) Core Doctrines`. Does this help explain the unexpected behavior?

claunia commented

2026-01-29 14:44:44 +00:00

@xoofx commented on GitHub (Oct 5, 2025):

Adding spaces for indentation before the third-level nested list element appears to resolve the issue. Specifically, I tried adding one extra space to the nested list items opening:
Does this help explain the unexpected behavior?

Good catch. I missed this detail when reading the issue in the first place. Actually, this is not unexpected but part of the indentation rules for list items in the spec.

@xoofx commented on GitHub (Oct 5, 2025): > Adding spaces for indentation before the third-level nested list element appears to resolve the issue. Specifically, I tried adding one extra space to the nested list items opening: > Does this help explain the unexpected behavior? Good catch. I missed this detail when reading the issue in the first place. Actually, this is not unexpected but part of the indentation rules for list items in the spec.

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Reference: starred/markdig#747