[BUG] Numbered lists that start at 1 are always in order even when they shouldn't

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Asking Claude to sort some items and output them as a numbered list causes it to use markdown which then causes the numbering to be off.

Steps to Reproduce

Use this prompt

❯ I have the following six items. I want you to group them in two categories (letters) and number the items chronologically (timestamp is an int) across all items (1-6).

For example if the first item in the second category is the first item chronologically, that one will be 1, and so on.

The items are

A 100 second
A 110 third
A 130 fifth
B 90 first
B 120 fourth
B 140 sixth

Give the output as

A:
n. message
m. message
...

B:
...

● A:
  2. second
  3. third
  5. fifth

  B:
  1. first
  2. fourth
  3. sixth

❯ Do it again, but I want the output as A = [n: message, m: message, .. ], B = []

● A = [2: second, 3: third, 5: fifth], B = [1: first, 4: fourth, 6: sixth]

What Should Happen?

The first output should have the same ordering as the second one

A:
  2. second
  3. third
  5. fifth

  B:
  1. first
  4. fourth
  6. sixth

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.1.81

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

_No response_