The following is my answer to a Quora question: “Can US citizens retire in Singapore?”
Singapore is not a place you can simply decide to retire to. The government does not simply give out long-term visit passes. This would work if the US citizen has worked or invested here, contributed to the economy, and then started the process to gain citizenship.
Citizenship must be secured before retirement, otherwise it will be denied. The reason is economic sense. If someone is not invested enough to take up citizenship during their productive years, it would be a loss on the economy to grant them the privileges of healthcare when they retire because they would not be a net contributor to Medisave.
Retiring here after the retirement age is still possible, but that would involve a substantial investment, such as setting up a family office, having significant funds parked here, or taking a major stake in a business with the intention of keeping it a going concern. This would make that person a net contributor to the economy, and citizenship is a reasonable option.
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