I thought they relaxed the exit control for NSFs last year?
"Giving an update in Parliament during the Mindef budget debate, Dr Ng said the Ministry has agreed to relax exit control measures for full-time national servicemen. Currently, they are required to apply for an Exit Permit whenever they travel overseas, regardless of the trip duration. With the change, they will be required to apply for Exit Permits only for overseas trips of 3 months or more."
http://www.channelnewsasia.com/stories/singaporelocalnews/view/196501/1/.htmlTo T/S: Actually, your S1 office shall be able to do everything for you. The previous system, unless things haven't changed, allowed servicemen to apply for EPs at the unit itself. So just inform your clerk that you're going overseas on your block leave, & let him process your applications accordingly.
If you do obtain an EP, don't lose it cuz must surrender it upon your return. If you're only required to provide "overseas notification" details, then prepare to submit certain info (travel destinations, return/departure dates, overseas contact numbers, etc.).
Separately, you must tell your immediate commander of your plans too.
With passports, most countries require they have minimum 6 months' remaining validity (i.e. beyond either your departure date, or intended date of entry, or its stated expiration date) or else they won't let you in. Same goes if you're a civilian. So make sure yours is updated.