Greetings @Sejones1 ,
Sometimes strange behavior can occur when you're trying to reset passwords on the free for teacher instance. I always ensure that you're double clicking the send email link after entering the email associated with the Canvas account. For some reason, double clicking is sometimes needed to actually send the password, and the reason for this isn't actually known.
I hope that helps! If for some reason that doesn't work, I recommend clicking the help link via your global navigation menu and clicking on the report a problem link and submitting the form explaining your situation. From there, someone from Canvas support will be able to provide you with additional information and support.
All the best,
Noah