Pre-departure window and exceptions
If no longer planning to work in Singapore, cancel within the week before departure. For departure on 10 February, submit from 3 February. Changing employer requires annual notification rather than cancellation; PR conversion or expiry needs no cancellation. Remaining after expiry still requires lawful stay.
Tax preparation
An employer seeks IRAS tax clearance at least a month before the holder leaves the job. A self-employed holder fulfils tax obligations at least a month before expected departure. These are different responsibilities, not a uniform employee-only process.
Cancellation and STVP
The holder or EA uses myMOM EP eService; cancellation is immediate and the pass and linked family passes cannot be reinstated. A holder remaining can request STVP up to 90 days from application. Show its emailed copy and valid passport when leaving and cut/discard the pass card.
Official source
Written independently from official MOM source material.

