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I really prefer ckeditor module than wysiwyg but Insert module support driving me nuts. With current versions (D7) insert does its job only on standard body fields, any other long text fields are out of its scope so I can't insert images.
I don't know js - Can someone look at insert.js file and update selection rules so insert.module will insert html in proper (active) ckeditor instances?
Or what other tools you are using for images and files insert?