Is an ITM option bought/sold to close in addition to being assigned?
The option is exercised. The option is converted into shares. That is an optional condition in closing that contract, hence why they are called options.
"From Pub 550: More or less stock bought than sold.   If the number of shares of   substantially identical stock or securities you buy within 30 days   before or after the sale is either more or less than the number of   shares you sold, you must determine the particular shares to which the   wash sale rules apply. You do this by matching the shares bought with   an equal number of the shares sold. Match the shares bought in the   same order that you bought them, beginning with the first shares   bought. The shares or securities so matched are subject to the wash   sale rules. You must match ""beginning with the first shares bought."" If only activity 1 & 4 happened, you'd have bought and sold stock with no wash sale. If you remove activity 1 & 4 from consideration because they are a ""normal"" or non-wash sale transaction, then the Activity 2 or Activity 3 trigger a wash sale. The shares in lot 1 are sold for disallowed loss, so the disallowed basis would be added to shares in lot 2 because lot 2 was purchased before lot 3. (hat tip to user662852 who had much better wording) Second example: Activity 5, 7, and 8 all together would not be a wash sale.   The addition of activity 6 creates a wash sale. The shares in Activity 5 are sold for a disallowed loss in Activity 7 & 8 because of the wash sale triggering purchase in Activity 6.   Activity 6 is where you add the disallowed basis because they are the ""first shares bought"" that cause the wash sale rule to be triggered." Option contracts typically each represent 100 shares. So the 1 call contract you sold to open (wrote) grants the buyer of that option the right to purchase your 100 shares for $80.00 per share any time before the option expiration date. You were paid a gross amount of $100 (100 shares times $1.00 premium per share) for taking on the obligation to deliver should the option holder choose to exercise. You received credit in your account of $89.22, which ought to be the $100 less any trading commission (~$10?) and miscellaneous fees (regulatory, exchange, etc.) per contract. You did capture premium. However, your covered call write represents an open short position that, until either (a) the option expires worthless, or (b) is exercised, or (c) is bought back to close the position, will continue to show on your account as a liability. Until the open position is somehow closed, the value of both the short option contract and long stock will continue to fluctuate. This is normal. "(See also the question How many stocks I can exercise per stock warrant? and my comments there). Clearly, at the prices you quote, it does not seem sensible to exercise your warrants at the moment, since you can still by ""units"" (1 stock + 1/3 warrant) and bare stock at below the $11.50 it would cost you to exercise your warrant.  So when would exercising a warrant become ""a sensible thing to do""? Obviously, if the price of the bare stock (which you say is currently $10.12) were to sufficiently exceed $11.50, then it would clearly be worth exercising a warrant and immediately selling the stock you receive (""sufficiently exceed"" to account for any dealing costs in selling the newly-acquired stock). However, looking more closely, $11.50 isn't the correct ""cut-off"" price. Consider three of the units you bought at $10.26 each. For $30.78 you received three shares of stock and one warrant. For an additional $11.50 ($42.28 in total) you can have a total of four shares of stock (at the equivalent of $10.57 each). So, if the price of the bare stock rises above $10.57, then it could become sensible to exercise one warrant and sell four shares of stock (again allowing a margin for the cost of selling the stock). The trading price of the original unit (1 stock + 1/3 warrant) shouldn't (I believe) directly affect your decision to exercise warrants, although it would be a factor in deciding whether to resell the units you've already got. As you say, if they are now trading at $10.72, then having bought them at $10.26 you would make a profit if sold. Curiously, unless I'm missing something, or the figures you quote are incorrect, the current price of the ""unit"" (1 stock + 1/3 warrant; $10.72) seems overpriced compared to the price of the bare stock ($10.12). Reversing the above calculation, if bare stock is trading at $10.12, then four shares would cost $40.48. Deducting the $11.50 cost-of-exercising, this would value three ""combined units"" at $28.98, or $9.66 each, which is considerably below the market price you quote. One reason the ""unit"" (1 stock + 1/3 warrant) is trading at $10.72 instead of $9.66 could be that the market believes the price of the bare share (currently $10.12) will eventually move towards or above $11.50. If that happens, the option of exercising warrants at $11.50 becomes more and more attractive. The premium presumably reflects this potential future benefit. Finally, ""Surely I am misunderstand the stock IPO's intent."": presumably, the main intent of Social Capital was to raise as much money as possible through this IPO to fund their future activities. The ""positive view"" is that they expect this future activity to be profitable, and therefore the price of ordinary stock to go up (at least as far as, ideally way beyond) the $11.50 exercise price, and the offering of warrants will be seen as a ""thank you"" to those investors who took the risk of taking part in the IPO. A completely cynical view would be that they don't really care what happens to the stock price, but that ""offering free stuff"" (or what looks like ""free stuff"") will simply attract more ""punters"" to the IPO. In reality, the truth is probably somewhere between those two extremes." You say that one property is 65% of the value of the two properties and the other is 35%.  But how much of that do the two of you actually own?  If you have co-signed mortgages on both properties, then your equity is going to be lower.  If you sold both properties, then your take away would be just half of that equity.  And while the 35% property may be less valuable, if you bought it first, it may actually have more equity.   It's the equity that matters here, not the value of the property.  With a mortgage, the bank is more of an owner than you are until you've paid down most of the loan.   You may find that the bank won't agree to a single-owner refinance.  A co-signed mortgage is a lot easier for them to collect, as they can hold either of you responsible for the entire loan.   If you sell the 65% property, then you can pay off any mortgage on that property and use the equity payout from that to buy out your relative on the 35% property.  If you currently have no mortgage, you'd even have cash back.  This is your fewest strings option.   Let's say that you have no mortgage now.  So this mortgage would be the only mortgage on the property.  It's not so much, as 15:65 is 3:13 or 18.75% of the value of the property.  That's more of a home equity loan than a mortgage.  You should be able to get a good rate.  It might reduce your short term profit, but it should be survivable if you have other income.   If you don't have other income, then seriously consider selling the 65% property and diversifying the payout into something else.  E.g. stocks and bonds.   Perhaps your relative would be willing to float you the loan.  That would save you bank fees and closing costs.  Write up a contract and agree to take assignment of the title at payoff.  You'll need to pay a lawyer to write up the contract (paying a modest amount now to cover the various future possibilities), but that should still be cheaper.   There's a certain amount of trust required on both sides, but this gives you some separation.  And of course it takes your relative out of the day-to-day management entirely.  Perhaps the steady flow of cash would provide what they need.   If your relative is willing to remain that involved, that can work.  Note that they may not want to do this, so don't get too attached to the idea.  Be prepared for a no.  This would be a great option for you, as you pretty much get everything you have now.  They get back the time meeting with you to make decisions, but they also give up control over those decisions.  Some people would not like that tradeoff.   The one time I was involved with a professional managing a property for me, the fee was around 7% of the rent.  If that fits your area, you might reasonably charge 5%.  That gives a discount for family and not being a professional.   There's a relatively easy way to find out what fits your area.  Look around and see what companies offer multiple listings.  Call until you find a couple that will do management for you.  Get quotes for managing your properties.  Now you'll know the amounts.   The big failing though is that this may not describe the issue that your relative has.  If the real problem is that the two of you have different approaches to property management, then making you the only decision maker may be the wrong direction.  This is certainly financially feasible, but it still may not be the right solution for your relationship.   If you get a no on this, I'd recommend moving on to other solutions immediately.  This may simply be too favorable to you. Depending on the day and even time, you'd get your $2 profit less the $5 commission. Jack's warning is correct, but more so for thinly traded options, either due to the options having little open interest or the stock not quite so popular. In your case you have a just-in-the-money strike for a highly traded stock near expiration. That makes for about the best liquidity one can ask for.  One warning is in order - Sometime friday afternoon, there will be a negative time premium. i.e. the bid might seem lower than in the money value. At exactly $110, why would I buy the option? Only if I can buy it, exercise, and sell the stock, all for a profit, even if just pennies. What keshlam said is correct. In bookkeeping terms, what you are doing is transferring value from some kind of cash account (which may in turn be backed by a loan) to an asset. Effectively, you are exchanging one asset for another. That asset you are exchanging to is the land that you are buying, which has some value, and which should end up on the asset side of your balance sheet. Unfortunately, particularly with fixed assets where no two ones are alike, such as land, it's often very hard to know the exact value unless and until you sell it. An appraiser can get you an estimate, but only sealing a deal with an actual buyer can get you an exact value, and at that point, the asset is no longer yours. You're correct in your implied point: Selling a cash secured put has less risk (in terms of both volatility and maximum loss) than buying the security outright. However, many brokerages don't allow cash-secured put writing in IRA accounts.   There are three reasons this tends to be the case: The put vs call assignment risk, is actually the reverse: in-the-money calls are more likely to be exercised early than puts. Exercising a call locks in profit for the option holder because they can buy the shares at below market price, and immediately sell them at the higher market price. If there are dividends due, the risk is even higher. By contrast, exercising an in-the-money put locks in a loss for the holder, so it's less common.