Is this a custom feature that you have implemented for the past version?
Can you provide better screenshots of the demonstrated functionality so that I can see whether this is a dialog or something else?
In the meantime please see this forum on a similar topic
Document Type icon for pdf.
The tool which you can test is called
<tool name="SPLinkManager" text="Insert Link" />
as you can see here - MOSSLinkManager.
If your question is how to get the file icon(before the file name) to display in the view mode for different file types , like word document, MS excel, pdf etc., file icons? - You can attach to the OnClientPasteHtml event, check the file type in the string returned by the args.get_value() method, add an image with the appropriate icon and insert the modified content via the args.set_value() method.
For SharePoint Editor, set the OnClientPasteHtml property in the \Program Files\Common Files\Microsoft Shared\Web Server Extensions\wpresources\RadEditorSharePoint\126.96.36.199__1f131a624888eeed\Resources\ListConfigFile.xml / ConfigFile.xml file:
\Program Files\Common Files\Microsoft Shared\Web Server Extensions\wpresources\RadEditorSharePoint\188.8.131.52__1f131a624888eeed\Resources
function OnClientPasteHtml(sender, args)
var commandName = args.get_commandName();
var value = args.get_value();
if (commandName == "DocumentManager")
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