The problem seems to be that the thickbox is not centering itself on the page properly. It’s showing to the far left and down the page. Mostly off the page in fact…
So when I click upload most people can’t see the box at all so they think nothing has happened. and it doesn’t throw an error because it actually worked just not the way you intended… hope this helps this is a great plugin concept.
Excellent plugin, just the simplicity I spent quite some time looking for in a ramdom image widget!
I also came across the issue where sometimes I’d add an image (uploaded or from the Media Library) and it wouldn’t get uploaded. After a bit of testing, it seems to occur when adding an image and having the LINK URL field set to “none”. If having clicked “file URL” or “attachment post URL” it seems to work fine.
Perhaps this is something that can be changed in a future version, as it causes some confusion – especially since the file/attachment URL field doesn’t have any effect on the output anyway.
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