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<<If I cash in AAA and BBB I can off set my capital gain with a capital loss. After an appropriate somber moment, I can reinvest in BBB, secure in the fact that my real win in the sale of AAA was offset in a real loss instead of a paper loss that would have been unseen by the Taxman.>>


As "mbwalker" points out, you're going to have "wash sale" problems with this transaction.

The sale of the AAA at a profit is certainly no problem.

And the sale of the BBB at a loss is also no problem UNLESS you have purchased additional shares of BBB either 30 days before OR after the date of the loss sale. If you did, then the loss on BBB will NOT be recognized for tax purposes, and the basis (or cost, for tax purposes) of the new BBB shares will be adjusted.

So if you do NOT wait the required 30 days before your re-purchase the BBB shares, you could have the worst of ALL possible worlds:

A taxable gain on AAA (on which you will owe tax); and
A wash sale on BBB, with no deductible loss allowed.

So be careful out there.
TMF Taxes
Roy Lewis
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