Macs not checking in

For us, the solution ended up being running:

sudo profiles renew -type enrollment

on each affected computer. But the root cause was us accidentally making the management account and the automatically created user account with the same name. 

So you have to actually get to each user and manually do something? its not the end of the world, but these folks are all over the place.  

We did, which was rough. There are some other tools you could employ if your issue is different than ours. There's a connection healing tool that jamf support walked us through that may work for you that didn't work for us.

We see this consistently. It’s more or less impossible to get devices to consistently check-in according to the check-in policy, which makes remote administration (we aren’t a school, folks aren’t on the same network, devices are sometimes across the country) completely unusable.

We are moving off of JAMF at first opportunity.

But the root cause was us accidentally making the management account and the automatically created user account with the same name. 

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this causes an issue?  I'd love to know more about this, since I think we've been setup that way for years!  do you have a link I can chase or anything where I can learn more?

Can you expand on that? You made your local admin account the same as the users account? Im confused on that wording. 

sorry I misunderstood - fresh eyes now and reading this properly - we are NOT making local admin account the same as the users account.