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For the sh script can you make sure that it is executable? Also you may need to set the shell to use */2 * * * * bash /www/script.sh Finally maybe add some loggintng in there? logger "starting script" logger "ending script" And then do logread -f to see if it ever starts

why not just schedule a task with the ducky to call home at set times? There are a ton of very simple programs to do reverse shells with varying levels of encryption/obfuscation that you could put in a place like %appdata% that would be easy enough to hide. https://technet.microsoft.com/en-us/library/cc772785(v=ws.10).aspx

I always have a kali live usb in my bag to boot of just in case.

I know this is a bit off, but it is possible to reset a password before login. I have used the "stick keys" bypass a lot go fix friend's forgotten password problems. Basically you boot off a live cd replace sethc.exe with cmd.exe. hit shift 5 times and pop admin shell. from there you can create/reset a local admin password. https://4sysops.com/archives/forgot-the-administrator-password-the-sticky-keys-trick/

What is the make/model of the laptop? I had a similar problem with a Lenovo laptop at work and this helped me: http://support.lenovo.com/us/en/documents/ht036206

A better place to store it might be ~/Library/Application Support/NameOfYourScript for two major reasons: this does not require admin privileges and is user-specific making it more dynamic based on the scenario ~/Library is hidden by default and is less noticeable to the user.