@Garrison Stribling,Thanks for posting in Q&A.
From your description, I know that you encounter an issue that two of the users cannot automatically get wi-fi policy after enrollment.
To clarify this issue, here are some steps you can refer.
1.Unenroll the problematical devices and create a new group with the two problematical users.
2.Assign the wi-fi policy and re-enroll the device using company portal.
3.Check whether the devices can receive the wi-fi policy automatically.
Please try above information, if there is any update, feel free to let me know.
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