Here's a few examples: https://www.sec.gov/spotlight/insidertrading/cases.shtml

Some further advice on the matter: https://www.bloomberg.com/view/articles/2018-08-12/the-10-la...

10 Laws of Insider Trading

1. Don’t do it.

2. Don’t do it by buying short-dated out-of-the-money call options on merger targets.

3. Don’t text or email about it.

4. Don’t do it in your mother’s account.

5. Don’t do it by planting bombs at a company and shorting its stock.

6. Don’t do it while employed at the Securities and Exchange Commission.

7. Don’t Google “how to insider trade without getting caught” before doing it.

8. If you didn’t insider trade, don’t forget and accidentally confess to insider trading.

9. If you are going to insider trade, do it in a company that is far away from a Securities and Exchange Commission office. Like, physically.

10. If you are already under a federal ethics investigation about your ownership or promotion of a stock, don’t insider trade that stock.

* https://m.xkcd.com/1053/

If they never make money, you’re fine. If they make a lot of money, it will get flagged ex post facto. Regulators then check if you or your family have any affiliations with the issuer; if they do, it’s flagged further. All of this typically happens automatically after companies’ stock prices move significantly.