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I have some text in a file copied to the clipboard via command line and I then wish to paste this content to a website.

cat file | pbcopy 

/usr/bin/open -a "/Applications/Google Chrome.app" 'http://google.com/'

(1) How do I paste to say google (if it's even possible)?

(2) Is it possible to open a different website, tab x amount of times and then paste?

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For sending keystrokes to a graphical application from a command-line program you can use xdotool (you may need to install it first). See the answer by Gilles to the question "How to send keystrokes (F5) from terminal to a process?" on Unix & Linux.

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