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To update, I was curious how the OCC would handle automatic exercise of an OTC stock. Normally an option is automatically exercised if it is .01 in the money at expiration based on the closing price on the stocks primary exchange, which is normally determined though a closing auction on that...

Normally the closing/settlement price (of the stock) used to determine automatic exercises of options (which can still be overridden) is based on a closing auction on the primary exchange. The question here is what price is used as this is now traded OTC.

You also said this If it's above, you won't be which is incorrect.

Not really correct. If a contract is .01 in the money, based on the closing price on the primary exchange, it will be automatically exercised. But the long holder can over ride this automatic exercise, so after hours movement matters. So you cant say you will/won't be assigned on a contract...

In your example, GFI, is not a penny option stock. The options must be quoted in at least nickel increments. It looks like you put a .02 bid in, so this price can't be displayed.

Not a data issue. I watch the overnight session in the SPX and VIX options. At times there are no quotes at all for some series (especially the back months) and at other times I will see "stub" quotes that are extremely wide with no bid.

What time did you look at these prices? Remember VIX options trade almost 24 hours a day. At times, during the overnight session, MM's will quote a very wide market. This can happen intermittently throughout the session. This wouldn't be a Schwab issue.

Here is how it is handled on the CBOE owned exchanges. Warning, lots of information. US Options Opening Process (cboe.com)

Op had the 52.5/55/57.5 Call Butterfly. So he was Long 1 52.5 call short 2 55 calls and long 1 57.5 call. There is no reason for a butterfly to involve puts.

Your December options will have their expiration dates accelerated to 11/18 and then they will be cash settled. You will in effect sell your 52.5 calls for 1.70 and the other part of your spread will expire worthless. See this OCC memo https://infomemo.theocc.com/infomemos?number=51250

Yep, 715pm ct for the options. Same as SPX options. The trick is finding a broker who allows trading in this session. Interactive Brokers is the only one I know of.

Technically options now expire on Friday evening, not Saturday. A change that was made several years ago. From the CBOE The expiration date for equity options is the Saturday immediately following the third Friday of the expiration month until February 15, 2015. On and after February 15, 2015...

Expire is not equal to stop trading. When something expires it is then worthless and can't be used. I think it is important to make this distinction to the OP. Even after options stop trading, they can still be used. They are still there and have risk/opportunity depending on whether you are...

Options DO NOT expire at market close. They may stop trading then, but they do not expire. You have until 530pm et ( or 1.5 hours after the market close) (most brokers will have an earlier cutoff time to meet this deadline) to exercise an out of the money option or cancel and automatic...

Agree with @Robert Morse. 3 month T bill yielding around what a box will get you. If you do buy a box, The spread on the individual options don't really matter. They will trade of the entire spread implied interest rates. You can go here to see recent box trades for guidance of what is...

This is the main reason I rarely use my IB account. The only time I will trade through them is for the overnight SPX session, which no other broker seems to offer access to.

No assignment risk here as OP was referring to SPX The question really is the order of liquidation. OP has ratio SPX spreads and a mixture of cash and stocks. Will IB buy in short SPX options, sell stock or remove the SPX ratio spread first if the margin requirement changes? The answer is...

All your questions are answered in the link @Overnight posted. Settlement value is posted here an hour or two after the opening Index Settlement Values (cboe.com) The settlement value is based on the opening price of the SPX options the morning of expiration. So, If you have Oct monthly...

SPY options trade until 415pm et Yes, you can wait to 4:10 to cover to avoid assignment, but your firm may close your position before this time if you don't have the funds to cover assignment. Check with them if they have a deadline. Vix options expire in the AM, although they are not...

The OP never mentioned futures, it was brought up by another poster. I was talking about options not futures. Everything I said was concerning options. But I agree, no real need to continue the conversation with you.