@carpentersm,

I am not sure how those two services function, so it is possible that something is interfering but you can try a few things:

1) After Assigning the Device to the Profile - Forget and Reconnect to the Network from the Chromebook (Did the Chromebook Reconnect as the Same Device Under his Profile?)

2) What Parental Controls Have you configured for the profile? Try removing some of the restrictions to see if the functionality comes back. Or Create a new profile with no restrictions and add the device there.

3) Try removing the Content Filters from the Profile, as it may be attempting to change a network setting that is forced by your school district.

4) Try Changing the overall DNS server that your network is using, such as moving to Google's 8.8.8.8 DNS server. These can sometimes provide a better connection, or solve problems with dropped packets.