Automations are triggered by individual records. So if three records change their status to “Overdue”, the Automation will run three times.
If you wanted bulk processing you’d have to add a “Find records” step that would give you a list of records which have an “Overdue” status. Since other Action steps cannot yet handle multiple record IDs at a time, depending on what you want to do with that list of records you may have to use the “Run a Script” action as opposed to the “Update a Record” action, for instance.
So this is the issue. I adjusted the automation to have an email sent to me. However, the e-mail was sent once even though, I expected multiple e-mails to be sent. In short, if the Automation had to run 3 times, it only runs 1 time.
So for the test, the status was already set to “Overdue” prior to running the automation. And yes, for the actual automation, I set up an e-mail test to see how many e-mails I would get. I only got 1 e-mail.
To clarify, a test of an automation step will run when you test it, regardless of whether the value recently changed or not.
For when the automation is turned on (and not in test mode), you didn’t answer whether the record values for “Status” were changed to “Overdue” before or after the automation was turned on.
If only one record’s value changed to “Overdue” since the automation was turned on, you’re only going to get one email.
If you’re saying “these three records weren’t ‘overdue’ until after the automation was turned on, but I still only received one email” then there’s some issue with your setup that needs some more exploration.