Recently it was discovered that the Sort by Column feature in the Display Settings of the Document Container did not actually sort the files or folders within the container. This information was passed on to SchoolMessenger. I recently received word that the bug has been found, fixed and the correction will appear in an update that is expected to be released in early May, 2018.
Other major outstanding content display issues that are still pending are:
1) Uploading an image with the same name does not really overwrite the older version of the image displayed on the page. This issue has also been resolved at SchoolMessenger, but is still in testing and will not be released until later this summer, hopefully before the start of the new school year.
2) Images that have transparent background components to them may not display as transparent when rendered in the content portlets of a page. This issue is still under investigation.