Have you set up work day templates? Your automation won’t know when to check-in/check-out your users if you haven’t set up work day templates and applied them to users/teams.
Also, automations you create on a particular day won’t trigger till the following day. Our service runs once a day (at 12 a.m. for the configured timezone) and therefore you’ll only see users enter your automation they day after you publish it.
For more information, see Auto Check-In/Check-Out Guide.