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What I have known and seen are Singaporeans who have obtained PR overseas and still keep their pink IC and enter/exit with Singapore passport at overseas port of entry. I suppose if these S'poreans eventually pick up a Canadian pp, nobody would know, until they renew their S'pore pp and make the declaration that they hold a foreign pp. They would enter/exit Canada with their Canadian pp and enter/exit S'pore with S'pore pp.
Are you one of them?
Not sure about Canadians, but for Australian PRs holders turned citizens, I found this loophole.
The main applicant of the OZ PR will have his PR visa cancelled after attaining citizenship. So any airlines in Singapore will not allow him/her to travel back to OZ on a Singapore passport with the OZ PR visa attached, even if it is not expired.
I also observe that the dependents of the main applicant who are issued the PR visas (with the condition that the dependents cannot initiate their first travel into OZ without the main applicant), their PR visas are not cancelled, even after they attain OZ citizenships.
OZ system screw up? These PR visas expires on their original expiry date, not when the citizenship is obtained.