I have heard that these devices can be problematic.

I think those IPads are still a bit photo challenged on AR.

Mary - I thought I read another post from someone who has had a problem with this as well, and the response was that it can't be done right now. I think the AR staff is working on this, but you might want to check with Bob Stewart to be sure.

I've done it a bunch of times, but I still haven't figured out how to upload photos.  

When you find the solution, this will be a good blog topic.

I don't think that you can.  I think others have been having problems and I don't think they've been able to fix this yet.  But, I may be wrong.

This issue has been my greatest source of frustration here on AR.

When I go to upload a new photo from my iPad, the system threatens to replace photos I've previously used on blog posts with the new photo.

The pop up message makes reference to uploading a photo with the same name.  The ability to name photos when uploading from my iPad has never existed, so I didn't want to take the chance of uploading a new photo and impacting my blogs.

There was a tiny period of time where I could safely upload photos from my iPad, but that disappeared with an update that occurred back in March or April.

After a number of emails back and forth with support and conflicting information, the final and unnecessarily snarky answer was to use a device other than an iPad.  The answer was not helpful.

Perhaps the new people in charge can bring back what once existed.