Fun fact: back in the day, Bingo Card Creator's "CMS" was a script which drove a mouse around the BCC swing applet, printed the card to a software PDF driver, opened it in Acrobat Reader, hit "Print Screen" on the keyboard, opened MS Paint, used dragging the mouse to hardcoded screen coordinates to crop the card, saved it as a GIF, and then put the GIF and PDF in subversion to be uploaded to the website later.
It worked well enough to justify learning Rails and Prawn to rewrite the whole thing server side, after which point I rm -rf'ed the directory that script was in and deleted the backup so that its vengeful shade would never trouble humanity again.
How much time did you lost over figuring out the recipe and scripting it?
Before I heard about configuration management, I had bash scripts to configure my server from clean state. I tried it locally hundreds of times to get every command right.
$150 for the script from somebody who did that thing for a living (apparently banks do this sort of hinge with regularity) and probably five hours lost to babysitting it and manually restarting when it hiccuped.
One of my daily tasks is to ssh into a remote Windows server, port forward the RDP port, connect to the local forward using remote desktop, close any dialogs about crashed drivers, open a java application that displays a KVM terminal connected to a serial port, and through the KVM control two separate devices with a series of magic key-presses to log into two accounts at the start of each day.
I automated this with Sikuli (http://sikuli.org/); the ninja feeling while watching it run was awesome (now it runs before I come into the office).
Sikuli made the job perversely fun, and the entire script is less than 100 lines of python. Highly recommended for any sort of GUI automation (though watch the dependency on Java 1.6; 1.7 doesn't work).
How about doing just that, to automate entering a password in Outlook so that emails can be collected from Exchange (which would require the mail user's password to be entered if Exchange was restarted) with Outlook running in a Windows VM on a Linux box, and a custom app processing the emails and POSTing them to an API on the Linux host, where they were processed to extract structured data out of attachments?
When looking at silent install files for ANSYS, I discovered that the install file simply records the keystrokes the user makes when a setup is recorded. That means that it also records any typos and backspaces. I must have really had trouble typing that license server name!
