Ok, here is what I ended up doing. I modified the Win32Site.pm so that the Win32Drop looks like the following.

sub Win32Drop
{
 # print join(',',@_),"\n";
 my ($w,$site,$msg,$wParam,$lParam) = @_;
 my ($x,$y,@files) = DropInfo($wParam);
 my $cb = $site->{'-dropcommand'};
 $site->Apply(-entercommand => $x, $y, 0);
 if ($cb)
  {
   foreach my $file (@files)
    {
     # print "$file @ $x,$y\n";
     $w->clipboardClear;
     $w->clipboardAppend('--',$file);
     $cb->Call('CLIPBOARD',$x,$y);
    }
  }
 $site->Apply(-entercommand => $x, $y, 1);
 return 0;
}
[download]

Basically all I did was change it so that it calls the "EnterCommand" before it processes a group of dropped files and "LeaveCommands" after. That gave me the necessary functionality.

Now, how do I get this change incorporated into the main codebase??