Yes, Win32::GuiTest can do this. I was interested by your post and have tried the procedure with the module and it works, though it's a bit of a fiddle to get it sat up right the first time around..

I used handler 1.5 to lookup the different widgets classnames, Control IDs, Texts, handles etc. A Must-have tool for this operation.

Here is some code for what I did. I've got this app that shows a registration nag-screen each time it starts. I wanted to fill in some dummy data and then close the nag window.

    use strict;
    use Win32::GuiTest qw(FindWindowLike GetWindowText SetForegroundWi
+ndow 
                          SendKeys GetChildWindows GetClassName GetPar
+ent);
    
      #Get our "mainwindow" - various search criteria can can be used.
    #FindWindowLike ($window,$titleregex,$classregex,$childid,$maxleve
+l)
    my @windows = FindWindowLike(0, qr/Iris License Registration/i,und
+ef,undef,);
      
      #Go through all widgets and sort out the ones we're interested i
+n
    for (@windows) {
          
          #Mainwindow has no parents..here we start
        if (! GetParent($_) ) {
             
              #dumps all children widget handles
            my @chld = GetChildWindows($_);
               
               #Dump handles to the two text-input fields we want
               #We lookup the classname for the widgets with handWler1
+.5, which is 'Edit'
            my @text_field;
            
            for (@chld) {
                    #Get handle to the empty text-input fields 
                if ( (GetClassName($_) =~ m/Edit/) && (GetWindowText($
+_) eq '')  ) {
                    push @text_field,$_;         
                }
            }
            
            #Now we have handles to widgets we wanna manipulate..
            #We insert text into the two input fields ("Registered To"
+ and "Licence Key")
             
              #Get text field we wanna manipulate in the foreground. A
+ctivates windows and widget..
            SetForegroundWindow($text_field[0]);
            
              #Hm..WaitWindowLike() wouldn't not work..Not exported an
+d not defined.. ??!
              #..instead we just wait a little, just in case..
            select (undef,undef,undef,0.50);
            
               #The "crux"..nice. Also we use 50 ms delay between each
+ key input.    
            SendKeys("Joe Doe",50);      
              #Go to next text-field, "serial nr field"...{TAB} key co
+uld have been used instead..
            SetForegroundWindow($text_field[1]);
            SendKeys("12345678acme{ENTER} ",50);
            last;      
        }
    }
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The module installs without problems with ppm on perl 5.8.3 build 809.