Pop up window not closing once the save button is pressed

We have a website where a client and punch in and out there work time for the day on a calendar.Once they press (AP) Add a Punch on the calendar a pop up window appears with some information of the current employee selected. At this point we should be able to key in a time and press save. This process works manually but when its ran with the automation software it does not work. Once save

is pressed the time entered disappears, the pop up window does not close and the time for the punch is not added to the calendar.

Crazy thing is that the test passes according to test complete even though the time was never added to the calendar once save was pressed.

A screenshot of my issue is attached.