I dropped the weights from my session reports to see if they'd automatically be organized in the correct order. All of my session reports start with the date of the session (i.e. "2024/04/12: The Rereckoning Part 1"). When viewing the relevant session reports category in my world, while the articles do show up in the left sidebar/table of contents in the correct order (earliest to latest), their ordering in the center is apparently random.
I haven't tested what happens if the category contains some articles whose titles don't start with numbers.Go to a category in Articles & Categories Management that contains articles whose titles start with numbers. Press "show additional options" in the right sidebar. Under Content Ordering, press Reset Order. View the category in your world.
I've added the manual weights back in, so the linked entity will no longer show them out of order. I can remove the weighting again upon request if needed for debugging.