How to send an arrow key in iTerm2
If you're trying to send an ↑ to the terminal, I've been able to accomplish this using the Send Text with &quot;vim&quot; Special Chars option and then using the escape sequence \u000d[A. For example, I'm using it to clear the console and repeat the last command, so the full sequence I'm sending is:
clear\u000d\u001b[A\u001b[A\u000d

This first writes clear to the console and then submits with Enter as \u000d. Then, ↑ is sent twice to get the command submitted before the last clear command, and Enter is sent again to submit the retrieved command.
Hope this helps you. Cheers!