Does the system calculate foreign work levy automatically?

No it will not.

In recent years MOM has taken over the calculation and will do auto deduction through GIRO. However, if you wish to do a one-off manual calculation, you can include the sum under Foreign Worker’s Levy found in ePayroll > File Generation > CPF Submission.

*Note: Only enter FWL if the Giro for the employee has not been in effect for the month yet.