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If I sell stock of Company-X at a loss and immediately buy the bonds of Company-X, am I allowed to deduct any loss on the sale of stock on my taxes, ie would this be considered a Wash Sale?

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This would not be a wash sale - bonds are "substantially different" from stocks, even of the same company.

Unless the bonds are convertible to ordinary shares, in which case they may "behave" enough like stock that they would be considered "substantially similar".

Even in that case, if you sold the bonds before the end of the tax year, the wash sale rules would not affect you. All wash sale rules do is transfer the cost basis to the purchased securities, at worst deferring any deductions for the initial loss.

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    Convertable would probably only be of note if the convertible was in the money – Jake Freeman Jun 2 at 20:49

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