Monday’s open could gap well past your strike. You wake up assigned at $450 on stock that opens at $440.

You may not have the margin to carry the share position.

The broker will close the position at the worst available price.

Close any short option that is within $0.50 of strike before the close on expiration Friday. The premium is small; the risk of pin is real (Hull, 2018, Ch 11).

On long options, decide Thursday whether you intend to exercise. Do not rely on auto-exercise to do what you "expected."

For broad-market index options like SPX (European-style, cash-settled), pin risk does not apply in the same form — the position settles to a cash value at expiration. This is one of the structural reasons institutional traders prefer European-style index options for short premium.

Exercise the call today, take ownership of the shares, capture the dividend tomorrow.

Or hold the call, miss the dividend (the stock price drops by approximately the dividend amount on the ex-date), and keep the extrinsic value.

Hard-to-borrow stocks — long put holders may exercise early to capture borrow rebate income.

Cash flow needs of the holder — rare but happens.

Mistakes — also rare, also happens.

Track ex-dividend dates on stocks where you hold short calls. Many broker platforms display "ex-div in N days" next to the symbol.

If your short call is ITM with less extrinsic value than the upcoming dividend, close before the ex-date.

Consider European-style options on cash-settled indices when you need a defined-risk position without early-assignment exposure.

You cannot transact in the option while the underlying is halted.

Your position sits frozen. Time still passes — theta still accrues.

Greeks become unreliable because there is no current market price.

When trading resumes, the underlying often gaps significantly. Your option position is now valued at the post-gap price — for better or for worse.

Avoid options on stocks prone to halts: small biotech, Chinese ADRs in regulatory limbo, distressed names, SPACs near merger decisions.

If you hold options on a halt-prone name, size smaller than you would on a large-cap.

Diversify across uncorrelated names so that one halt does not dominate your account.

Your put is now $20 ITM.

Your stop-loss limit (if any) executes at $20+ premium — well past where you wanted out.

You absorb the gap, not a planned exit.

Close discretionary positions on Friday afternoon if your thesis is not playing out — the weekend offers theta cost, gap risk, and no upside in the form of trading days.

For positions you must carry through a weekend: size for the worst-case gap, not the average move.

On Fridays going into binary events (earnings reports scheduled for Monday morning, weekend Fed appearances, election windows), reduce exposure proactively.

For binary events generally, prefer defined-risk structures: spreads, condors, butterflies. Not naked positions.

A 5× oversized position turns a normal weekend gap into a margin call (Chapter 5).

For long premium into earnings: assume IV crush. Your trade must be right enough directionally to overcome the vega loss. The implied move tells you roughly how big the stock needs to move to break even on a long straddle.

For short premium into earnings: you are explicitly betting against the implied move. You will be right ~60% of the time. The 40% where you are wrong can be catastrophic. Iron condors or iron butterflies are preferred over naked short strangles.

Track implied move vs actual move on the underlyings you trade. Build the table over time. The pattern is informative.

Pre-emptive sizing. The position you can carry through a liquidity event without forced action is the right size.

In low-VIX environments, do not assume the spread will stay tight. Quote tightness is a feature of the regime, not the option.

For credit spreads with both legs deep ITM at expiry, close before expiration day to avoid pin/assignment risk under low liquidity.

Cross-asset correlations spike toward 1 in crises (Taleb, 2007).

Beta hedges underperform when the systematic move is dominated by idiosyncratic shocks.

"Tail hedges" priced cheaply often pay off less than expected when the actual tail event has different dynamics than the historical reference.

Stress-test the hedge under a 5-sigma move and under a "regime change" where correlations break.

Do not rely on a hedge that has not been tested in actual market stress.

For retail traders, this argues for keeping things simple — risk-defined positions, sized small enough that no hedge is needed.