When there are few checkbox items in RadListBox (i.e. there is no scroll bar), checked items cannot be unchecked. The issue is reproducible in iPAD.

RadListBox allows to declaratively bind the Text and Value properties of the ListItems, e.g:

<telerik:RadListBox runat="server" DataTextField="Text" DataValueField="Id">

Unfortunately, this is not possible for the ImageUrl property.

My Suggestion: please allow to also bind the ImageUrl declaratively as known from other controls, e.g:

<telerik:RadListBox runat="server" DataTextField="Text" DataValueField="Id"
    DataImageUrlField="..."

// and maybe even like this:

    DataImageUrlFormatString="..." DataImageUrlFields="...">