..Andy, .. you must sell and you can only repurchase the security after 30 days, whether it is in your unregistered or registered account..........Just thinking out loud here, if one sells at a loss in their cash/margin account then the loss is carried forward. The funds ( $ 5,000. ) from the sale can now be transfered into into your TFSA.....The 30 day Rule to - me is kinda iffy here. The TFSA is moniterd for the right contribution of $ 5,000 but if the TFSA is all Tax free money with one not being able to claim any losses or gains with in, then this leaves one to Question if the rules should be the same given their not. .. Traps7