Workflow not sending email to first reviewer but sends to everyone else

I have a criteria workflow that is working fine except for one small problem. The first person in the workflow does not get notified. If they login and approve, the content continues through the workflow and everyone else is notified. I can even reject it all the way back to the original contributor, and then that contributor sends it on to that first person in the workflow and then they get an email. It's just that initial email when the workflow kicks off doesn't go out.
Nothing showing up in our ECM error logs or email logs. If you look at the workflow info, it says that first person was notified. I've also tried changing who that first person is and what they can/have to do and it makes no difference.
Any suggestions?

Is the first person in the Entry Step or the second step of the workflow?

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