When booking through online travel websites, how do I know if the airline will treat multi-flights as separate trips or a single trip?

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This will be treated as a single trip (leg), because you are actually booking a flight from SIN to SFO with one stop. So you can (and are expected) to check-in for both flights all the way to SFO.

If there would be two separate "boxes" with these two flights, then they would be treated as two separate legs in the booking.

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