I'm planning on doing something like this myself with one of my projects, and 
the way I plan on trying it out is by using:

    -(NSButton *)standardWindowButton:(NSWindowButton)b;

for each NSWindowButton of the NSWindow, find a reasonable visual gap to the 
left/right of one of the buttons, and then add my own to their superview.

Now that I think of this, I might also need to consider above/below gaps for 
vertically-placed buttons.

Try this out and let us know how it works.

>I'd like to draw a padlock icon in a window title bar, similar to the 
>way Safari does when it's displaying an https URL.  And I'd like to 
>be able to respond to clicks on the padlock by displaying security 
>information.  Is there a supported way to add a button to a window's 
>title bar?
>
>Thanks,
>-- 
>Jim Matthews
>Fetch Softworks
>http://fetchsoftworks.com
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