I created a workflow based on date but it is not sending updates as expected

I created the following workflow and I cannot seem to figure out why it is not sending the updates as expected.

The row that should have triggered it is below:

I can't seem to figure out what I have set wrong here. I just want it to send the rows that have today as the upgrade date to the people listed in the contacts at the bottom (all are members of my organization and have the sheet shared to them.

Anyone have any ideas?