: Does it count as long term gains if you buy and sell more shares of an existing stock holding? I'm a little uncertain on how capital gains tax applies to this scenario. Will it be considered a long term or a short term gain?

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In the first case, you have a long-term capital gain when you sell the 50 shares for a higher price than when you bought them. Rebuying the shares in 3. at a lower price has no tax
consequences.

In the second case, the answer will depend on which shares you sold. If the shares
are of a mutual fund, you can also use the average cost per share and have a mix
of long-term and short-term gains.

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In the first scenario, the 50 shares you sold are subject to long term capital gains taxes in the event you do not buy anymore. However, if you repurchase those 50 shares at a lower price than what you sold them, within 30 days, it essentially doesn't count that you sold in the first place. See page 59 of IRS Publication 550.

In the second scenario, it all depends on which shares you sell, which may or may not be confusing to sell. Most trading houses have the option for you to select how you want to sell your shares (First In/First Out, Last In, First Out, etc). In the case that you sell the first 100 shares you bought, then it would be considered a long term gain (because it was a few years ago). Assuming you recently bought those 50 share (say 3 months ago) and then sell 100 shares, 50 being from your purchase several years ago and 50 from your purchase 3 months ago, then you would pay long term capital gains on 50 shares and short term capital gains on the other 50.