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Email workflow

Hello,

I have a workflow setup that allows for emailing certain records (invoices, pos, sos, etc) to multiple customers by hitting a button that stays "email", if that button has already been pressed it changes to "resend email". I would like the work flow to recognize if the email has been sent outside of pressing the email button. How can I add a condition that considers messages sent. I would like the button to change to "resend email" if for example, bulk invoicing has happened that sent triggered the emails. Is there a way to add a condition that is something

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