When an annotation range gets extended around a list, adding a bullet point at the end of that list creates a second </translate> tag, which then breaks the VisualEditor workflow (since the tags are not well balanced anymore).
This is reproduced by the following test case:
!! test Extended annotation marker should not get duplicated !! options parsoid={ "modes": ["selser"], "changes": [ ["li", "after", "<li>Second item</li>"] ] } !! wikitext <translate> * First item</translate> !! wikitext/edited <translate> * First item * Second item </translate> !! end
which renders instead
<translate> * First item</translate> * Second item </translate>