SS4: WYSIWYG Image Issue After Files Migration

Upon upgrading a SS3 site to SS4.1 and migrating the file system, I see that images in WYSIWYG areas do display fine, but have lost their association with the original file, so if you resize a WYSIWYG image it doesn’t create a new resampled image, and just stretches the previous resampled image (you also can’t adjust the image alignment or alt text etc).

Is that the expected behaviour? Or should it be finding the original image and created a new resampled version as it would before the upgrade?

(I guess setting legacy_filenames: true would work around it, but just wanted to check that’s the only way to keep older WYSIWYG images fully working, as I understand it isn’t recommended.)