Perhaps I am misreading your question but if mean using an image previously uploaded in your forum or IP.Content etc then when making the new post click the 'My Media' button and it will open a 'popup' with all your files/images you have previously uploaded
As mentioned .. likely am misreading your post so apologies if that is the case
that only works when something is uploaded to a forum or gallery. items uploaded to prior articles don't show in my media.
also, when adding the actual article image you can't click my media. you can click it in the article and add an image to the article, but thats NOT the ARTICLE image. its a pretty important distinction.
if you try linking to the other image after clicking upload it fails too.
would love to see this ability. using the ccs_media folder from front end is a useless really.