Steps to reproduce:
1. Insert two lists
<ol>
    <li>test1</li>
</ol>
<ol>
    <li>test2</li>
</ol>
2. Copy the first list
3. Insert one more list item in the second list and paste the first list
Expected:
<ol>
    <li>test1</li>
</ol>
<ol>
    <li>test2</li>
    <li>test1</li>
</ol>
Actual:
<ol>
    <li>test1</li>
</ol>
<ol>
    <li>test2</li>
    <li>
    <ol>
        <li>test1</li>
    </ol>
    </li>
</ol>

The desired behavior cannot be achieved out of the box with the content provider from this KB article, because the paths to the images are passed to a generic handler.
The main reason it can't be achieved at the moment is that the latest moment of the page life-cycle of the FileBrowser.ascx dialog, when the user can set the FileExplorer's InitialPath is before the Page_Load event, but the path to the preselected in the Editor item is passed in the Page_Load event and the initial path is reset internally.

Currently when pasting an ordered list from MS Word, the RadEditor’s lists converter does not take into account the list’s items numbering. 

The following list
 
5.	Li1
6.	Li2

will be converted to

1.	Li1
2.	Li2

Whe you're trying to add an image with "#" or "&" symbols in it's title - image displays as corrupted in image editor.

When dragging items from an outside source into a RadEditor, be it text, image, video, etc. The API used to perform drag & drop is lacking. For example, an overlay needs to be shown over the top of the iframe element for the editor, whereas I would like to perform the drop at a specified area where I drop - not where the cursor is located.