Automation Isn't Working



I am having trouble with my automation. I have a set of rules to assign colleague contact when certain criteria is met. I've noticed that one is not working and another is working too well where it is assigning this person to all my rows. Please see my screenshots below. I'm not sure where there error is in my rules.

Automation rule that is not working:

Last run date is dated in March even though I ran it for my whole sheet today:

My sheet that shows the other colleague contact assigned:


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