General user help and bug reports for Playground Sessions for Mac
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Same thing happens to me. I just go to click around to other things in the program (like: my playground, or sometimes I act like I'm going to play one of the lessons again) then eventually go I back to the dashboard and it loads the progress.
I am a newish user (about 10 days) so I am a recent software install. I am seeing this behavior as well. When all sections of a module are completed I click Bootcamp menu, the module does not reflect completion (green checkmark). I click the module again, all sections are complete, click Bootcamp menu and now the module reflects the green checkmark. I have not tried clicking around to other menus to see if the status updates, I just use these steps.