Automation won't send again

Hello!

I'm at my wits end and can't figure out why this won't work - the automation is intended to send an email out on the date in the Notification Date column (which is always a Monday) and to send it to contacts in three columns - Agenda, Review Transcript/Follow Up Items, Others to Notify.

See below for how I have it setup - I'm assuming it might be with the "Run once" trigger, but I can't figure out the best way to set it up then. The weird thing is that if you look, it says the automation ran - but no one received emails. We've all checked junk/spam, we know the domain is not blocked for our organization. The two date columns are set as Date columns and there are no formulas there, just typed in dates.

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