Small Optim,

Replace all those SendKeys with one:

Win32::GuiTest::SendKeys('%y');

I actually did pretty much the same save I have a separate script that that lives for 2 minutes who's sole purpose in life is to kills off that popup window. In the calling application I call Win32::Process::Create as a detached_process just before causing the window to popup.

p1:..code..
p1:Win32::Process::Create(,'allow_outlook_send.pl',,,DETACHED_PROCESS,
+)
p2:started, on loop look for window
p1:access outlook
p1:hang on output
p2:found window, click yes (till yes is available)
p2:exit
p1:got output
p1:..code..
[download]

TM