Resending a Row with attachments

I have an automation set up to send an "update"/"notify" a specific person when a new row is added. I didn't select any advanced options. We didn't want him notified EVERY time a small change is made to a row, but there are times he has updated significant information and he essentially wants to resend that row to himself.

He is not a licensed user so he can't right click on the row and send himself an email or an update. So as a work around I added a checkbox and an automation that anytime he checks it, it will send him an email. Great right? Problem is no associated attachments are showing up in that email. I have gone into advanced settings and selected all the columns including comments and attachments.

Anyone know of a better work around than what I have done here, and/or how to have attachments show up in the notification email he is receiving? I'm thinking maybe it's because no NEW attachments were added to the row...but don't know if that's the hiccup (no attachments showed up on the original automated New Row email either).

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