@theopenem_admin
Thanks! I think the inventory bug is what was causing the issue I saw - I was not seeing the deployment had happened and thought the failure was with Checkin. When I went to the Computer level and ran the commands I always ran the Checkin first, and then looked at the inventory. I assumed Checkin at group is what wasn't working, but probably had; the reality is the push had happened but the inventory hadn't updated until I ran Inventory on the Computer side.
Thank you for checking into it!