Your options agent will get assigned on a Friday it didn't plan for

Most trading agents treat an option like a stock with a funny price. Brokers don't. Three things catch agents out:

1. Dividend early assignment. If your agent is short an in-the-money call and the time value left in it is less than the next dividend, the holder will usually exercise the day before ex-dividend. Your agent then delivers the shares and gives up the dividend (or owes it, if it ends up short the stock).
2. Pin risk. If the stock closes within about 1% of a short strike on expiration day, nobody knows until after the close whether you'll be assigned. That's an unplanned position over the weekend.
3. Auto-exercise. The OCC exercises expiring longs that are $0.01 or more in the money unless you opt out. A cash account that can't pay for 100 shares per contract gets a margin call or a forced sale on Monday.

Then there's the margin side. A naked short put or call needs the FINRA Rule 4210 requirement: the premium plus the greater of 20% of the underlying minus the out-of-the-money amount, or 10%. Your broker's options approval level also has to allow the strategy at all.

options_risk_check checks all of this before your agent sends the order: margin requirement, approval level, dividend assignment, pin risk, auto-exercise cash and net Greeks. It costs $0.01 per call, with 25 free calls a day on a free key (the get_api_key MCP tool gets you one in-session).

MCP: agent-financial-advisor.agent-financial-advisor.workers.dev/mcp?src=devto2
Examples: github.com/mytomclinic/agent-financial-advisor/tree/main/examples