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bhamjoel
New Member

Should I sell my oldest stock first or my newest stock first?

I have a good number of shares, all in the same company. I want to sell some of them. Should I sell the shares that were obtained recently first - or the shares I bought some time ago? I know there are tax consequences surrounding this. That is why I ask.
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2 Replies
RayW7
Expert Alumni

Should I sell my oldest stock first or my newest stock first?

It depends, on how long you have held the stock(s).  The tax rate can vary dramatically between short-term and long-term gains. Understanding the capital gains tax rate is an important step for most investors. As a general rule if you have a profit from the sale of a stock you would want to sell those stocks that you have held for over 1 year first, (long term gain).  The tax on long term gains are typically less than short term gains.  

 

Capital gains are taxed according to how long you've held a particular asset – known as the holding period. Profits you make from selling assets you’ve held for a year or less are called short-term capital gains. Alternatively, gains from assets you’ve held for longer than a year are known as long-term capital gains. There are specific rules and different tax rates applied to short-term and long-term capital gains. In general, you will pay less in taxes on long-term capital gains than you will on short-term capital gains.

 

As previously mentioned, different tax rates apply to short-term and long-term gains. However, if your investments end up losing money rather than generating gains, those losses can affect your taxes as well. However, in this case, you can use those losses to reduce your taxes. The IRS allows you to match up your gains and losses for any given year to determine your net capital gain or loss.

 

Short term gains will be taxed at your ordinary income tax rate.  Long term gains for tax year 2020 will be taxed from 0%, 15% or 20% depending on your filing status and income. 

 

If you don't specify with your broker which stocks to sell they will default to selling the stocks you obtained first. 

 

 

 

 

Should I sell my oldest stock first or my newest stock first?

The above reply ignores the issue of what you paid for the shares  you choose to sell.

You'll have to do this analysis yourself.

You can sell any lot by informing the broker ahead of time what you want to do.

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