Photos won't rotate

I just took a picture with my iPad 2.  It was sideways so I rotated it.  Looks fine now but won't send in email that way.  Does anybody know why?  My friend just gets the sideways photo.

Earlier today I emailed myself the 'screen shot' I took of the photo in the upright position and it mailed correctly. So I sent it on to my friend.
Which still begs the question...Why does the Photo App have an 'Edit' if it's not going to work?
And why do we have to take pictures of our pictures to get the correct rotation?

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