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Suppose I have a stock ABC of 1000 shares whose ex-dividend date is May 20 (Wednesday) and I sell 500 shares after the market closes on May 19 (Tuesday) during the extended hours of trading, say at 4:14pm EST. Do I still get the dividend for 1000 shares? Or just for 500 shares?

Similarly, if I instead bought 800 shares on May 19 (Tuesday) after 4pm, say at 4:14pm, will I get dividend for the 1800 shares or just 1000 shares?

In addition, is buying/selling before 9:30 am on May 20 during the extended hours, say at 9:18am making any difference?

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You will receive the dividend for shares you bought after-hours the day before ex-dividend, and won't for shares you sold then. So the answers in your case are 500 and 1800.

You can confirm this by observing that a stock price does not suddenly drop at 4pm the day before ex-dividend. The drop occurs overnight between the end of after-hours and the start of premarket trading on ex-dividend day.

See here:

Orders executed during an after hours session are considered to have been executed during the day's traditional session for settlement and clearing purposes. This can be an important for dividend investors when buying a stock on the ex-dividend date. If you buy on or after the ex-dividend-date in regular trading, after hours trading or premarket trading, you do not qualify for the dividend. However if you buy the day before, even in after hours trading, you still qualify.

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Suppose I have a stock ABC of 1000 shares whose ex-dividend date is May 20 (Wednesday) and I sell 500 shares after the market closes on May 19 (Tuesday) during the extended hours of trading, say at 4:14pm EST. Do I still get the dividend for 1000 shares? Or just for 500 shares?

You must own the shares on the ex-dividend date to get the dividend. The date is a day of the month not a time during the day so in this example, you only own 500 shares on the ex-div date.

Similarly, if I instead bought 800 shares on May 19 (Tuesday) after 4pm, say at 4:14pm, will I get dividend for the 1800 shares or just 1000 shares?

The ex-div date is May 20th. You own 1,800 shares before the ex-div date so you get the dividend on all 1,800 shares.

In addition, is buying/selling before 9:30 am on May 20 during the extended hours, say at 9:18am making any difference?

Again, it's the date not the time that matters.

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