End Year Stock Haversting

[Dsf4man]

I understand that one may balance stock losses against capital gains, but I don't really want to sell any of my stocks that are performing well. My question is, whether it would advantageous to sell my underperforming long term stocks at a loss to lower my tax liability? 

[Anonymous_]

See https://www.irs.gov/taxtopics/tc409

You can use capital gains to offset your capital losses and then use up to $3,000 in net capital losses to offset all other types of income.

[fanfare]

If your stock is performing well, there would be no loss to take advantage of.

If your stock shows a loss but you feel it will recover, and want to deduct it, you have to wait 31 days before repurchasing that stock.

In my experience, stocks go up in January, so by the time you can buy it back it is already up.

@Dsf4man 

[Dsf4man]

So it appears that the only way to reduce my tax liability is sell  gains to offset losses. E.g. sell some Apple stock at a gain and sell some of my marijuana stock at a loss. And should I want to repurchase Apple I'd have to wait 31 days after the sell. Does this rule apply if perhaps in a Roth IRA? 

[fanfare]

• A) Remember you can only deduct 3,000 of net losses each year.

• B) If you sell a gainer and a loser your net is zero you haven't changed your tax liability. If you are forced to sell a gainer for any reason, or other wise impelled to take profits, only then does it makes sense to sell a loser. (this ignores the issue of selling to cut your losses and redeploy capital.)

• C) Some robots will sell gainers and losers just to keep your porfolio rolling over.

• D) When you purchase in an IRA, the wash sale rule requires you to wait 31 days to sell that security from a regular account if you want to deduct a loss from that sale in the regular account.
   Within the Roth account there are no taxes, so there is no tax liability to worry about.

@Dsf4man 

@Dsf4man