Pages that fall into category 'Pages with broken file links' aren't automatically pulled after those links are made to work, either by uploading the relevant pictures or otherwise. The problem got worse after the change in 1.27 whereby InstantCommons functionality isn't working as documented any longer and losing connectivity to Commons can potentially add tons of pages to that category.
One would expect that at least a Ctrl-Shift-R (or equivalent) into that category page would force a refresh with the current list of offending pages, but it doesn't.
Further, users are typically referred to maintainance scripts to work around the problem (refreshlinks.php, rebuildall.php, etc.) but more often than not those scripts don't help either.