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I am sure its something I am doing wrong but this is the message I saw

phpBB Debug] PHP Warning: in file [ROOT]/ext/sitesplat/imgur/event/listener.php on line 63: fopen(): Filename cannot be empty
[phpBB Debug] PHP Warning: in file [ROOT]/ext/sitesplat/imgur/event/listener.php on line 64: fread() expects parameter 1 to be resource, boolean given

And where the preview was supposed to be I saw

Invalid URL ()
Ok, I did a little experimenting, and it seems to be giving this error only with large files. I'm going to do further research to see if I can solve it.

In the meantime, maybe try for files that aren't as big? I know that's not a solution really. Many of us want to use photos right from our phone camera, and they're naturally going to be quite large.

I'll see what I can figure out.
If the photo has more colors and details, there would be more data and the file size would be larger. Maybe the iPad takes photos that hover right around the threshold for what is allowed. So some work, some don't.

But I don't intend for there to be a size limit. Hopefully you won't have to think twice about this in the future. I'm on the case.
Update: Error fixed, file size limit increased
It was a file size issue. There was a limit of 2MB for the photo uploading, and some of our pictures were just over that amount. So the file wouldn't get uploaded, and then you'd see the "URL not found" error, because the image didn't exist on the server where it was meant to.

I boosted the upload limit a little, and larger photos are going through fine. Enjoy your photo uploading everyone. Can't wait to see more pics of your pumpkins, costumes, decorations, art, collectibles, etc.