Can one choose to not settle an ITM option at expiry?

OP is using taxes and tax rates as a rationale for asking whether there's a way to prevent long ITM options from being executed. It stands to reason that he considers it a taxable event in his trading strategy (i.e., he plans to close out the shares he receives at expiry).
why oh why take such a stupid pin risk ??? the market might open 20% lower on monday and what then .... if you just sold the call nothing of that kind of risk. Things can be simple unless you start making them complicated !
 
Agreed. I don't understand the tax rationale behind this question on any level, this just being one of those levels.

But since you asked the question: for the same reason people write naked options with stop losses and then hold them overnight (where the stop loss can't trigger). I mean, everyone's done that at some point in their trading life, right? Not just me? :)
 
I've discussed this with my broker (TradeStation); by their rules, there's no way to file a standing "do not exercise" order. It has to be done for each specific trade that you do not want exercised, and has to be requested before 4:15pm - within 15 minutes of the market closing.

(I was ITM by 0.01, and didn't feel like paying the exercise fee.)

Hey Blue! Nice seeing you posting!

How is TradeStation by the way? Could I open an account and use their trading platform for free like TOS offers? I want to branch out from TOS just to see what else is out there, I haven't tried much else, TOS has been flawless, but I'd like to see other stuff.
 
20-25 years ago I had covered calls that never got exercise. They were at the money when they closed or maybe one cent above...They didn't want to pay for the commission (which was like $25-30. back then).

I also try and watch my income. I have shared before on this forum, "it's not what you make, it's what you take home"!! I do NOT want to go above a certain amount...To keep my Obamacare. It makes sense to me, but others think I'm crazy. Let them...I know what I'm doing. Worked it out with my CPA also...Even he is doing the SAME thing (I gave him the idea)!! Grow your assets, not your income...Nothing to see here IRS, keep walking. Below is a summary of why I don't grow my income...

Who is eligible for a subsidy?
So who are the nearly 9 million people who were receiving premium subsidies as of mid-2019? Subsidy eligibility is based on income (ACA-specific MAGI): You have to earn at least 100 percent of the federal poverty level (139 percent of the poverty level in states that have expanded Medicaid), but not more than 400 percent of the poverty level.

Source: https://www.healthinsurance.org/obamacare/will-you-receive-an-obamacare-premium-subsidy/
 
Hey Blue! Nice seeing you posting!

How is TradeStation by the way? Could I open an account and use their trading platform for free like TOS offers? I want to branch out from TOS just to see what else is out there, I haven't tried much else, TOS has been flawless, but I'd like to see other stuff.

Hey, @.sigma - good to be back! Life Happened to me for a while, but it all worked out... I didn't really even get hurt by this crash, which tells me I was doing the right thing.

TS has a really great plat in terms of doing chart-based work, in some ways the best I've seen. But on the other hand, the reliability of their software is total shit: it'll crash (some of my friends who use it report it doing so twice a day), and then you have to do all sorts of silly fiddling with blowing away caches - of which there are several - and occasionally the entire configuration, which then requires rebuilding your desktop and anything else you've customized.

Oh, and that's their new and improved (and it really is) version.

Other bits about them: reasonably decent fills; absolutely shitful and clueless tech support; even their trade desk support is questionable (so I've learned to call several times and ask in several different ways. It's been an education.) Overall, as I understand it, they're about average. Give'em a call and see what they offer you!
 
OP is using taxes and tax rates as a rationale for asking whether there's a way to prevent long ITM options from being executed. It stands to reason that he considers it a taxable event in his trading strategy (i.e., he plans to close out the shares he receives at expiry).


So rather than exercise and then be forced to sell the stock and take a short term capital gain the OP is asking if they can have it go away worthless...??

Stupidity is more contagious than Corona
 
I am going to exercise my right not to wait 24 hours and show why the answers are not on target.

I believe there is a margin situation created if you exercise your position. Suppose it is the last day of expiry with a strike price of 100 and the closing price is $100.10 You are long 10 options The broker automatically exercises. Monday morning you are long 1000 shares. You now have margin situation. If you close the position that day you need to have 25k excess cash or equivalent not to be in violation. A worst scenario is that there is bad news on Monday. e.g the stock trades e.g. 80. Now you are out 20k.

That is my recollection
Ah ok that helps. I thought that auto-close meant auto-settle in ca$h. They actually deliver the shares.

It's not like oil or gold; no, they will not drive up to your house with an armored truck with bullion or tanker with oil.

I'm still not sure if I can let an ITM option expire--with neither cash settlement nor execution. Just let it die; no payment, no shares.
 
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