Exercise and assignment
If you own an option, you hold the right to exercise it: to buy at the strike with a call, or sell at the strike with a put. Whether you exercise is entirely your choice.
If you sold an option, you carry the matching obligation. When a holder exercises, someone on the short side is assigned, and it may be you. That is not a choice, and it can arrive without warning.
When early assignment happens
American-style options can be exercised any day before expiration, which sounds alarming and mostly is not. Exercising early destroys the option’s remaining time value: the holder gets intrinsic value only, when selling the contract would have captured both.
So early exercise is usually irrational, and it stays rare. It becomes rational in a small set of situations: a deep in-the-money option with almost no time value left, a short call before a dividend, and occasionally a deep in-the-money put when interest rates make holding cash worth more than the remaining optionality.
The dividend case
This is the one to watch. If you are short a call that is in the money and the stock is about to pay a dividend, the holder can exercise the day before the ex-dividend date, take the shares, and collect the dividend.
The test is simple arithmetic: if the dividend is larger than the time value remaining in the call, exercising is worth more than selling, and the assignment is likely. A $0.75 dividend against a call with $0.20 of time value left is very likely to be exercised.
For a covered call this is usually just an early exit at your strike. For a short call without shares behind it, it means suddenly being short stock and owing the dividend.
At expiration
Most assignment happens at expiration and follows a simple rule. Anything in the money by a cent or more is automatically exercised by the clearing house unless the holder instructs otherwise. Anything out of the money expires worthless.
If you are short and your option finishes in the money, expect assignment. Shares arrive or leave over the weekend and appear in the account on Monday, along with the cash.
Pin risk
The genuinely uncomfortable case is a short option that finishes almost exactly at the strike. You do not know whether you will be assigned until after the close, and the holder can decide either way.
That leaves you with an unhedged stock position over the weekend that you did not choose and may not have wanted. On a spread it is worse: one leg assigned and the other expiring worthless converts a defined-risk position into a directional stock position, and Monday can open anywhere.
Managing it
Close, do not hold. Buying back a short option for a few cents removes all of this. Most of the money lost to assignment surprises would have been saved by a cheap closing trade.
Watch ex-dividend dates on short in-the-money calls, and roll out or close if the dividend exceeds the remaining time value.
Only sell what you can deliver. A cash-secured put means assignment is simply buying stock you already agreed to buy at a price you chose. Sold without the cash behind it, the same contract is a margin call waiting to happen.
Assume it will happen at the worst time. Any position whose outcome depends on not being assigned is not a position you control.