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I’ve read so many answers and questions on this forum regarding this issue but never read anything about how often one can use this 96hr visa free stay in Singapore? I am a female Russian citizen, 22 years old (it’s relevant, as there is some law that doesn’t easily allow Russian unmarried women of 18-45 years of age to travel freely).

If I plan to fly with my German boyfriend from Malaysia to Singapore on 29th of April, stay there for 1 night and fly to Bali on 30th of April and then in 14 days, on May 13th fly back to Singapore from Bali and stay there for 2 nights and leave at 2am on May 16th to Berlin, do I need a visa or can I use twice the 96 hours free transit for CIS citizens? I know some say it depends on the passport control officer to either let you in or not, but if they do, and you show all the relevant documents (plane tickets, hotel reservation etc) do you think it should be fine?

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Singapore's Immigration and Checkpoints Authority says only that:

Nationals of the Commonwealth of Independent States (CIS), Georgia, Turkmenistan and Ukraine

If you are in transit to or from any third country, you may be eligible for the 96-hour VFTF if you have a valid onward air ticket departing within 96 hours. You may enter Singapore by any mode of transport but must depart Singapore by air.

There are no restrictions given on how frequently anyone can use this facility. But you must convince the immigration officer that you are not trying to live in Singapore on a pass that does not permit it (like a study pass or employment pass). Based on what you say about your itinerary, this should be very easy for you to show, so I would not expect trouble with obtaining the 96 hour transit pass.

Timatic, the database which airlines use to verify travel documents, also states that you should be fine:

Visa required, except for Nationals of Russian Fed. with a confirmed onward ticket for a flight to a third country within 96 hours under the Visa Free Transit Facility (VFTF). They must have documents required for the next destination.

Providing you have your Schengen visa or EU residence permit, (you didn't mention it) then I expect no problems with this itinerary.

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I did trip by bus from KLIA (Malaysia) to Singapore as a transit on 22/04/19 and I've had flight ticket to Jakarta (Indonesia) on 23/04/19. I'm holding Russian citizenship. On the border (Malaysia/Singapore) Singaporean immigration officer asked to follow in their office and I spent about 15 minutes while senior officer checked my data/passport/bookings and he has asked questions to me to prove that my end destination is Indonesia. The important is to have your route trip that is showing that Singapore is only transit destination. As example tickets should be Russia-Thailand-Singapore-Indonesia, but not a Indonesia-Singapore-Indonesia.

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    Singapore's web site lists Commonwealth of Independent States (Содружество Независимых Государств) instead of Russia individually. See the other answer. – Michael Hampton Apr 27 at 3:19

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