Have you considered Win32::GuiTest? I've used it in the past to automate funky, dare I say flaky old applications.

I have heard about that module. When I run ActiveState ppm (Perl Package Manager), I don't see it as a package option for the latest AS version. There a lot of reasons why that could happen. I haven't investigated why that is yet.

I am hoping to find a tool that does most of the work, with me just writing some small amount of extra code. I am hoping for an option better than Win32::GuiTest. If "GuiTest" winds up being "the answer", then likely follow-on questions will involve complicated build problems that Active State has not solved.

Update: I installed the cpan module from Active State. And lo and behold, installation of Win32::GuiTest appeared to work. I will investigate this module further.

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Define better? The question you posted had a list of things you had to do in order to automate a couple of programs. The module I suggested provides convenient ways to achieve this. The module documentation is pretty clear on where to get a PPD file, how to build from source. I don't recall having issues with either method when using AS perl, or simply using cpan/cpanm. A quick search shows AS do offer a version, though perhaps not built for your version of AS perl. Make life easier in yourself, switch to Strawberry perl or just follow the documentation for building it yourself ;).

1 + 2 = Marshall Win

1 https://metacpan.org/pod/distribution/Win32-GuiTest/lib/Win32/GuiTest/Examples.pm#eg/waitwindow.pl

2 https://metacpan.org/pod/distribution/Win32-GuiTest/lib/Win32/GuiTest/Examples.pm#eg/pushbutton.pl

There are a whole bunch of automation programs. One person suggested AutoHotKey. I am open to any solutions. My initial testing with Win32::GuiTest indicates that this can be a lot more complicated than it sounds.

I had a positive experience with Win32::GuiTest. If you want to go this way start by getting a handle to the window you are interested in. The manual shows this: my @found = FindWindowLike(0,"title-regex");. And the t/01_basic.t test script does it this way:

# Create a notepad window and check we can find it
system("cmd /c start notepad.exe \"README\"");
my @waitwin = WaitWindowLike(0, "readme|README", $class_re);
is(@waitwin, 1, "There is one notepad open with README in it");
my @windows = FindWindowLike(0, "readme|README", $class_re);
is(@windows, 1, "The same from FindWindowLike");
is($waitwin[0], $windows[0], "The two windows are the same");
 
# Find the edit window inside notepad
my $notepad = $windows[0];
my @edits = FindWindowLike($notepad, "", "Edit");
is(@edits, 1, "Edit window found within notepad");
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I do not have any experience with the AutoIt3,that harangzsolt33 suggested, nor with AutoHotKey. I am sure they will do the job equally well. However, an all-Perl solution has benefits. The tricky part, recalling from my experience, is to wait for the windows to show and then make sure that the usual windows blabbering via popups will not get in the way of what window focus and arrangement you want.