Salesforce Email Alert to Fire when Date = Today()

Question

I'm having a tough time trying to get this email alert to fire. Correction, I can get it to fire, but not when I want. I have the following fields: Last Login and Last Login Target Date.

Use Case: I need to alert the account owner if a user hasn't logged into our app in 30 days. I query into our app database on a weekly basis to get the 'last login' dates for each account. I then data load the CSV into our every account's Last Login dates on the account object.

I have two workflow rules with one field update for one, and one email alert for the other

1. When Last Login is changed, Last Login Target Date is updated. i.e. WFR: IF( ISCHANGED(Last_Login__c) , True, False) and Field Update: Last_Login__c + 30
2. When Last Login Target Date = Today, email acount owner. i.e. WFR: IF(Today() = Last_Login_Target_Date__c , True, False) and email alert: 'Send Email to Account Owner'.

The idea is that if I keep uploading the same Last Login date via data loader, the Last Login Target date will stay the same until a different date in Last Login is updated.

However, today, when TODAY () did, in fact, equal Last Login Target Date no email alert went out.

I'm wondering why the workflow rule isn't firing when the WFR for the email alert is = TRUE.

Screen Shot for ref: Any help would be greatly appreciated, and I'm happy to explain in more detail if needed.

Thanks!