Re-Entering Singapore from Malaysia

Did you read threads in visa category? We have advised similar cases many times already.

Next time spend more time on reading various threads as most of questions are answered multiple times.

Now, coming back to your query, read my answer below:

1. There is no remaining days as such, once your friend left Singapore. So, the remaining days are nullified once your friend departs.

No issue at departure time.

2.  There is no guarantee that on his/her arrival, he or she will be allowed to enter again. There would be higher possibility, immigration officer will ask the reason for his or her second visit in short span of time. He or she has to give a rationale to visit second time (don't say for waiting interview result or coming here for sightseeing, they can easily track down his/her last stay which was 22 days, more than enough for sightseeing a tiny country).

There is no question of that remaining days, it's already invalid after he or she left Singapore.

He or she must have to show return ticket of his/her final or next destination along with accommodation details in Singapore including contact number of hotel or place during his/her stay.

He or she may get 30 days or much lesser (may be a week or so) or may even deny to enter. So, mentally be prepared for all possible result. Good luck

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If an EP is already applied for, it is o.k. to say so when asked for reason of stay. But just waiting for job offers does not give him the right to stay in Singapore longer.
Rather than hoping for a visa extension through the back door by temporarily visiting Malaysia, your friend could contact ICA before his trip and ask for advice on how to handle the situation - but then he needs to give a valid reason other than job search.
That said, after a week of absence and if it is the first such incidence, the risk of problems is low (but not zero!).

Hello, thanks heaps for your advises. In relation to the accommodation and contact number, he is staying at my place. Can he provide my contact details instead? Thanks a lot