A SOLUTION: I awoke during the night recalling a method I'd seen in the Win32Util module about "always keep ontop". Its a bruteforce way of forcing your Tk Window to the front and *keeping it there* even if you maximise other windows. See the amended code below. (Note: setting the optional flag to 1 forces it ontop, setting it to 0 disables it.

The mind of a programmer never sleeps! :-)

## Insert these into main
use Win32::Sound;
use Win32Util;

## subroutine for dying
sub dying {
    my ($error) = @_;
    
    if (!$error) {
        $error = "(none given)";
    }
    my $text;
    $text .= "\n\nTARsync Error:\n\nFailed during:\n$message\n\nReason
+:\n$error";
    if ($poperr) {
        my $box = new MainWindow(-title => "TARsync failed!",
                    -bg => 'yellow',
                    -bd => 4,
                    -relief => 'ridge');
        $box->overrideredirect(1);
    
        my $label = $box->Label(
                    -textvariable=> \$text,
                    -bg=> 'yellow',
                    )->pack(-fill=>'both',
                        -padx => 40,
                        );
        Win32::Sound::Play('SystemExclamation');
        my $ok = $box->Button(-text => "OK",
                    -command => [ sub{$box->destroy;
                            exit;
                            } ]
                    )->pack(-padx => 20,
                        -pady => 20
                        );
    
        $box->withdraw;
        $box->Popup;
        Win32Util::keep_on_top($box, 1);
        MainLoop;
        }
}
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