There was a similar issue lately. Read the part at the really end:
https://github.com/jarmo/RAutomation/issues/69

Jarmo Pertman
-----
IT does really matter - http://itreallymatters.net


On Tuesday, August 20, 2013 4:10:32 AM UTC+3, Dan wrote:
>
> If it's a javascript popup you don't need rautomation and you shouldn't 
> have this problem.  Check out 
> http://watirwebdriver.com/javascript-dialogs/ or 
> http://rubydoc.info/github/watir/watir-classic/frames.
>
> On Monday, August 19, 2013 6:27:31 PM UTC-4, Champ wrote:
>>
>> Hello,
>>
>> I use rautomation frequently within my watir scripts to work with popups. 
>> It works really well when I have an open active window and browser open and 
>> I use the send_keys functionality.
>>
>> However,  it is failing when I run the scripts on a remote machine 
>> minimized as a window, It just stays at the popup where it is supposed to 
>> send the keys.
>>
>> I am suspecting it is something to do with activating the popup window, 
>> but not sure.
>>
>> Any inputs?
>>
>> Eg script:
>>
>>   @ie.button(:text, "logoff").click_no_wait
>>   logoff_win= RAutomation::Window.new(:title => "page title", :adapter => 
>> :autoit)
>>   logoff_win.WinWait("page title",'',7)
>>   logoff_win.WinActivate("page title")
>>   logoff_win.send_keys('{ENTER}')
>>
>>
>> -champ
>>
>

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