My specific issue is that two adjacent lists end up getting combined together along the process of docx --> html --> markdown.

As in:

1. Item 1
2. Item 2
3. Item 3

1. Item 1
2. Item 2
3. Item 3

in the docx end up converted as:

1. Item 1
2. Item 2
3. Item 3
4. Item 1
5. Item 2
6. Item 3

one way around this is to pass in ignore_empty_paragraphs=False into mammoth.convert_to_html so that the blank line between the lists ends up as <p></p>, which then causes markdownify to separate the lists properly. However, the DocxConverter does not allow for passing any options into mammoth.convert_to_html other than custom style maps.

Possible related issue

• Missing new lines between adjacent lists matthewwithanm/python-markdownify#245