Assign a task is not sending email

I am currently working on building an approval workflow. There are several Assign Task actions in a row. For testing purposes, I have set them all to send to myself. They all are configured pretty much the same. The problem is that the first action assigns the task and sends the email as expected. The second assign task looks like it assigns the task, but it doesn't send the email. Email doesn't appear to be blocking it and I am not sure what else it could be.