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Can someone kindly clarify the following couple of questions for me please, thank you Looking at America style options first I understand they can be exercised at any time. So if sell a call option (write) for a strike price of $55 when the stock (spot) price is $45 with an expiry of 30 days (just to give some numbers) Question 1: If the stock never reaches its strike price during this 30 days the holder of the option (buyer) 'can not' exercise this option (as the contract terms have not been met). Therefore the contract cannot be assigned, is this correct ? Even thought the option holder (buyer) cannot exercise (until strike price is reached) they could sell their option contract (with less days left on it), at what ever market premium they can get for the option at that time. (which is not the same as an option being exercises/assigned) ? Question 2: When it comes to European style options which can only be exercised at at expiration (small time window) again using the numbers above (but on an Index) If the index goes goes well above is strike price 15 days from expatriation, but then goes back down below the strike price at expiration, I assume the option expires worthless. As the buyer of the option was 'unable to exercise it when it went past the strike price' is the above also correct ? However as above even though the holder of the option could be exercise this European style option exactly when they wanted, they could sell the option on (with the remaining time until expiry and same strike price), is that also correct ? Thanks very much in advance

Just wondering if anyone has ever had success negotiating with TOS to reduce/remove the $19.95 fee that TOS charges for assignment and exercise. If so, what kind of arguments worked best? I agree with Kim that we shouldn’t have to negotiate to get the best rates. However, I greatly prefer TOS’s platform to anything else out there. I’ve been using tastyworks for a while now too, and their platform is only ok, but it’s still a work in progress, and they still charge $5 for assignment/exercise. The reason I’m asking - and not considering IB’s $0 assignments- is because I’m evaluating a couple of candidates for wheel trades (sell puts, get assigned, sell covered calls, get assigned, rinse/repeat). Since the cycle involves two assignments, the $40-ish total fees at TOS is cost prohibitive. And I refuse to use IB because of their auto-liquidation algorithm - I don’t want to have my account blown up if I get assigned on a couple of different positions one night and don’t have a chance to close things out within 10 minutes of the market opening. So if I could get TOS to come down or eliminate their assignment fee, that would be great. Otherwise I’m stuck with TW - I suppose I’ll get more used to their platform over time, but everything about their apps makes me feel like I’m playing an arcade game from the 80s. And not in a good way.... Any input is greatly appreciated!

@Yowster or others, I'm hoping to get some advice. I occasionally trade unofficial hold through earnings (HTE) calendars and have run into a recurring issue. After earnings, sometimes the price jump in the stock results in my calendar becoming deep in the money. When I try to close out the deep ITM calendar, the market makes it very difficult or impossible for me to close out at a reasonable price. For example, this recently happened to me on RHT. I had an 82C calendar spread March 31 short / April 7 long and at the close before earnings on March 27 the stock price was $82.32. About an hour after the open on March 28, RHT stock was at $86.93. So my 82C were $4.93 ITM. But the mid-price to close out the spread was in a kind-of 'backwardation' (yes, I know that isn't the exact right term, but the situation seems similar). The mid for the short leg was $5.00 and the mid for the long leg was $4.90, so a debit of $0.10 to close the spread. Paying a $0.10 debit to close the spread (or even closing at $0.00) seemed unreasonable given that if I held the short leg through expiration, any premium to close the short options would be gone and hopefully the long option would recover some premium ($0.10 to $0.15 based on my review of other RHT options in different time periods). So I held the spread through expiration and got assigned. I closed out the position the following day using a combo stock / option order on TOS. I'd like someone who has done a number of these HTE trades to help me understand: 1. Has this ever happened to you? How would you recommend closing the trade when the price to close out the calendar spread is "way off" from what seems reasonable (e.g., having to pay a debit to close)? 2. If I do hold through expiration and get assigned, am I still 100% covered by the long option? In other words, will the changes in the long option prices offset changes in the short stock position exactly? I'm guessing the answer is no, but I haven't really looked at this yet and am not sure the best way to model it. I appreciate the advice. Thank you!