When a Record Matches Conditions does not trigger when conditions are met

I have a table where I want an email per record to be sent when a record matches conditions. For example:

Contact Email is NOT Blank
and Check Box 1 is Checked
and Check Box 2 is Checked
and Contacted is Empty

The Actions are: Send an Email and Update the record with a Check in the Empty.
However, the automation only ran for the test record out of the 15 records matching the criteria.

If you’re testing the automation it will only run for one record. You have to turn the Automation on for it to run for all/any record in the table. Note that if the records already met the conditions at the time the Automation was turned on then the Automation won’t run for those records.