Covered call and put options as separate trades
Yes, if the call expires worthless, leaving you with stock. Then you can exercise your put when the stock goes below put strike price.
I do this often with shares that I own - mostly as a learning/experience-building exercise, since I don't own enough individual stocks to make me rich (and don't risk enough to make me broke). Suppose I own 1,000 shares of X.  I don't expect my shares to go down, but I want to be compensated in case they do go down.  Sure, I could put in a stop-loss order, but another option is to sell a call above where the stock is now (out-of-the-money).   So I get the premium regardless of what happens.  From there three things can happen: So a covered call essentially lets you give up some upside for some compensation against downward moves.  Mathematically it's roughly equivalent to selling a put option - you make a little money (from the premium) if the stock goes up but can lose a lot if the stock plummets. So you would sell call options if: "For personal investing, and speculative/ highly risky securities (""wasting assets"", which is exactly what options are), it is better to think in terms of sunk costs. Don't chase this trade, trying to make your money back. You should minimize your loss. Unwind the position now, while there is still some remaining value in those call options, and take a short-term loss. Or, you could try this.  Let's say you own an exchange traded call option on a listed stock (very general case). I don't know how much time remains before the option's expiration date. Be that as it may, I could suggest this to effect a ""recovery"".  You'll be long the call and short the stock. This is called a delta hedge, as you would be delta trading the stock. Delta refers to short-term price volatility.  In other words, you'll short a single large block of the stock, then buy shares, in small increments, whenever the market drops slightly, on an intra-day basis. When the market price of the stock rises incrementally, you'll sell a few shares. Back and forth, in response to short-term market price moves, while maintaining a static ""hedge ratio"". As your original call option gets closer to maturity, roll it over into the next available contract, either one-month, or preferably three-month, time to expiration. If you don't want to, or can't, borrow the underlying stock to short, you could do a synthetic short. A synthetic short is a combination of a long put and a short call, whose pay-off replicates the short stock payoff.  I personally would never purchase an unhedged option or warrant. But since that is what you own right now, you have two choices: Get out, or dig in deeper, with the realization that you are doing a lot of work just to trade your way back to a net zero P&L.  *While you can make a profit using this sort of strategy, I'm not certain if that is within the scope of the money.stachexchange.com website." "The two dimensions are to open the trade (creating a position) and to buy or sell (becoming long or short the option). If you already own an option, you bought it to open and then you would sell it to close. If you don't own an option, you can either buy it to open, or sell it (short it) to open. If you are already short an option, you can buy it back to close. If you sell to open covered, the point is you're creating a ""covered call"" which means you own the stock, and then sell a call. Since you own the stock, the covered call has a lot of the risk of loss removed, though it also subtracts much of the reward possible from your stock." "One alternative strategy you may want to consider is writing covered calls on the stock you have ""just sitting there"".  This will allow you to earn a return (the premium from the calls) without necessarily having to give up your holding. As a brief overview, ""options"" are derivatives that give the holder the right (or option) to buy or sell shares at a specified price.  Holders of call options with a strike prike $x on a particular security have the right to purchase that security at the strike price $x.  Conversely, holders of put options with a strike price of $x have the right to sell that security at the strike price $x.  Always on the other side of a call or put option is a person that has sold the option, which is called ""writing"" the option.  If this person writes a call option, then he will be obligated to sell a certain amount of stock (100 shares per contract) at the strike price if that option is exercised.  A writer of a put option will be obligated to by 100 shares per contract at the strike price if that option is exercised. Covered calls involve writing call contracts on stock that you own.  For example, say you own 100 shares of AAPL, and that AAPL is currently trading for $330.  You decide to write a Jan 21, 2012 call on these shares at a strike price of $340, earning you a premium of say $300. Two things can now happen: if the price of AAPL is not at least $340 on January 21, then the options are ""out of the money"" and will expire unexercised (why exercise an option to buy at $340 when you can buy at the currently cheaper market price?).  You keep your AAPL stock plus the $300 premium you earn.  If, however, the price of AAPL is greater than $340, the option will be exercised and you will now be required to sell the shares you own at $340.  You will earn a return of $10/share ($340-$330), plus the $300 premium from the call option.  You still make out in the end, but have unfortunately incurred an opportunity cost, as had you not written the call option you would have been able to sell at the market price, which is higher than the $340 strike price. Covered calls are considered relatively safe and conservative, however the strategy is most effective for stocks that are expected to stay within a relatively narrow price range for the duration of the contract.  They do provide one option of earning additional money on stocks you are currently holding, albeit at the risk of giving up some returns if the stock price rises above the strike price." The risk situation of the put option is the same whether you own the stock or not.  You risk $5 and stand to gain 0 to $250 in the period before expiration (say $50 if the stock reaches $200 and you sell).   Holding the stock or not changes nothing about that.  What is different is the consideration as to whether or not to buy a put when you own the stock.  Without an option, you are holding a $250 asset (the stock), and risking that money.  Should you sell and miss opportunity for say $300? Or hold and risk loss of say $50 of your $250?  So you have $250 at risk, but can lock in a sale price of $245 for say a month by buying a put, giving you opportunity for the $300 price in that month.  You're turning a risk of losing $250 (or maybe only $50 more realistically) into a risk of losing only $5 (versus the price your stock would get today). "I would think that a lot of brokers would put the restriction suggested in @homer150mw in place or something more restrictive, so that's the first line of answer. If you did get assigned on your short option, then (I think) the T+3 settlement rules would matter for you.  Basically you have 3 days to deliver.  You'll get a note from your broker demanding that you provide the stock and probably threatening to liquidate assets in your account to cover their costs if you don't comply.  If you still have the long-leg of the calendar spread then you can obtain the stock by exercising your long call, or, if you have sufficient funds available, you can just buy the stock and keep your long call.  (If you're planning to exercise the long call to cover the position, then you need to check with your broker to see how quickly the stock so-obtained will get credited to your account since it also has some settlement timeline.  It's possible that you may not be able to get the stock quickly enough, especially if you act on day 3.) Note that this is why you must buy the call with the far date.  It is your ""insurance"" against a big move against you and getting assigned on your short call at a price that you cannot cover. With the IRA, you have some additional concerns over regular cash account - Namely you cannot freely contribute new cash any time that you want.  That means that you have to have some coherent strategy in place here that ensures you can cover your obligations no matter what scenario unfolds.  Usually brokers put additional restrictions on trades within IRAs just for this reason. Finally, in the cash account and assuming that you are assigned on your short call, you could potentially could get hit with a good faith, cash liquidation, or free riding violation when your short call is assigned, depending on how you deliver the stock and other things that you're doing in the same account.  There are other questions on that on this site and lots of information online.  The rules aren't super-simple, so I won't try to reproduce them here.  Some related questions to those rules: An external reference also on potential violations in a cash account: https://www.fidelity.com/learning-center/trading-investing/trading/avoiding-cash-trading-violations" "Yes, you can insure against the fall in price of stock by purchasing a put option.  You pay for a put and if the price of the share falls below the ""strike price"" of the put, then you can exercise the put.  On exercise, the person who sold you the put contract agrees to buy the stock for the strike price, even though that strike price is higher than the market price.  You can adjust the level of insurance by buying put options at higher or lower prices, or buying fewer put options than shares you own (leaving some shares uninsured). Alternatively, you can minimize your risk exposure by investing in an index or other fund, which gives you partial ownership in a large number of shares.  That means on any given day, lots of shares do worse and lots of shares do better.  You can reduce the need for insurance by purchasing a lower-risk, lower-growth financial product." Well, yes -- you've implicitly made many assumptions (such as that the embedded option has longer maturity). The important thing to consider is when this option pays out; the premium will obviously be adjusted.  For a concrete example, consider an equity option-on-an-option. The outer option has strike 110, the inner option has strike 100 (spot = forward = 100). Then the inner strike pays out when spot_T &gt; 100, but the outer option has zero value there; the overall option only pays out if spot_T &gt; 110, reducing the structure to a call option with strike 110.