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If you let your domain expire, it will enter what is known as a "grace period" or "redemption period". What happens is when a domain name expires it goes through a 40 day grace period, and then a redemption period of possibly 5 days to a few months. The time frame can be different for each registrar. Once this period is complete, then your domain name will be available for repurchase. It is not possible to transfer your domain name it is in this redemption period.
So, if you wish to transfer your domain name, it is best to do it a few weeks before your domain is set to expire.