I believe you’re encountering this:
Here’s how I came across it: Ordered lists: Each nested level must start with "1" to be understood as a new list item.
My general workaround is to add a blank line before the sub-item so Obsidian will interpret it as a list item and not just a continuation of the previous line (which was a different list item).
So like:
1. [ ] #task Task 1 in 'numbered_list_items_standard'
1. Sub-item 1
2. [ ] #task Task 2 in 'numbered_list_items_standard'
2. Sub-item 2
3. List item in 'numbered_list_items_standard'
It’s not pretty but it works:
