I disabled all plugins including the optimizer. and not running any caching. unless wordpress caches some elements by default? didn’t see anything while digging tho… 

okay. no, nothing internal for wp – just wanted to make sure that optimizer wasnt caching js or something…

so your problem now is only IE in compatibility mode??  not even sure what that is for…

The issue is only with IE.

If you clear all temporary internet files, cookies, etc from IE then log back in the site, the AD file button works but only once.  As soon as you post a picture you need to clear all temporary internet stuff again and restart browser for the button to work again.

NOTE: If I enable compatibility mode in IE, the AD file button works all the time. But this is not a solution for me as using compatibility mode creates many more problems with the site.  I am simply mentioning it incase it helps narrow down what the issue could be.

Mr Papa said
https://simple-press.com/support-forum/sp5-plugin-topics/tinymce-not-available-in-ie9/page-8/#p113681

I’ve given this a go and the same issues arise. I haven’t disabled my theme but I’ve disabled all of the [edit: theme] JS on the forums page and the same problem still occurs – only in IE.

I’m not using Compatibility Mode (awesome way to break basically any website using JS in my experience) nor were the other users that reported the problem.

at a loss frankly… handful of these and quite difficult since I cannot duplicate on 6 or 8 test sites (diff servers, setups, configs, themes, plugins, etc) either…

did google compatiblity mode a bit and yeah, pretty much everyone said avoid…  not sure if they meant compat mode or IE…   anxiously awaiting IE 10 later this month and extremely hopeful that MS finally decides to pay even a little attention to standards…

dunc, do yo have a link?