When uploading photos to a place either through the back end or front end, only the first image (featured image) shows up in the media gallery. All other images I upload to that same place are not shown in the media gallery.
To make the images show up I have installed a plugin “Media from FTP” which scans the upload folder and adds the missing photos to the media gallery.
The downside to this is that all the new images found are shown as “Unattached” so it looks like they aren’t being used on the site, even so they are attached and live on the site.
I believe I may have found a bug where any image other than the first one is not added to the database or linked to a place.
(Also the featured images that make it into the Media Gallery have (no title) whereas the missing images found through “Media from FTP” have their titles set to the same as the file name. This could be by design though I’m not too sure.)