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Wiki Selling TSLA Options - Be the House

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Options take 3 days to settle.

Options only take one day to settle. Stocks take 2.

From the link you posted:

"Exceptions​

You should be aware of a couple of exceptions:
  • When you close a short sale at a loss, the tax law treats the transaction as occurring on the settlement date. See Last Day to Sell."
My understanding is that applies to short stock sales, not short option sales.

Here is what Tastyworks says:

Last Day to Close Positions for 2021 Tax Reporting​

LONG STOCK/ETF SHARES, LONG OR SHORT EQUITY OPTIONS, AND BROAD-BASED INDEX OPTIONS​

Trade Date: Friday, December 31, 2021

Profits or losses for long stock/ETF shares, long or short equity/ETF options, and Broad-Based Index Options* (i.e., SPX, NDX, VIX, etc.) report based on their trade date. As a result, any long stock/ETF share position, individual option, or option spread position must be closed by Friday, December 31, 2021, if you wish to report the gain or loss for the 2021 Tax Year.
 
Decided to let my 880 BPS ride over the weekend, even though they were at 75% after 24 hours.

Also added 1250/1300 BCS for next week at one of the run ups - they were sitting at 30% at end of day.

Let’s see what next week brings…

1130 cc/lccs
1150/1200 880/830 IC
1250/1300 BCS

I’ll start to consider managing the positions if we break 1100
 
Options take 3 days to settle. I called Fidelity when I did our taxes in April because I really wanted that loss on my 2020 taxes, but they explained that the settlement date is what they use for OPTIONS, not the trade date. I was led to believe that stocks are different (but don't know about short vs long).
yeap; i had same issue last yr (dec 2020)... for tax purposes, settlement date was used in BOTH stocks and options; only gains REALIZED in 2020 were taxed

OPTIONS:
1640297638020.png


i traded these 5 STO/BTC on dec 31 and got $40k credit, but i couldn't understand why i did not receive tax receipts from TD

then i noticed that the settlements were jan 4

$40k is this year's (2021) income even though the money was received in 2020

STOCK:
1640298311173.png

same thing for stocks; i did NOT receive tax receipts for the dec 30 sale due to settlement date of jan 4

$228k is this year's (2021) income even though the money was received in 2020
 
really helped me keep my cool and trade on reason rather than emotion (much tougher than I anticipated tbh).
It really isn't all there is to this, but at some point it sure does seem like it. Keep the emotion under control and be able and willing to (at times) do nothing or not do too much. I sort of doubt that anybody has completely eliminated emotion from their trading, but maybe sometimes we can keep it on a leash.

I know that I frequently read this thread, or a few pages of the main thread; put it together with my own thoughts and get some balance to the emotions when they're trying to run amok. It seems that a shared community of like minded folks can all be more successful together, than any of us can be on our own.
 
yeap; i had same issue last yr (dec 2020)... for tax purposes, settlement date was used in BOTH stocks and options; only gains REALIZED in 2020 were taxed

OPTIONS:
View attachment 747566

i traded these 5 STO/BTC on dec 31 and got $40k credit, but i couldn't understand why i did not receive tax receipts from TD

then i noticed that the settlements were jan 4

$40k is this year's (2021) income even though the money was received in 2020

STOCK:
View attachment 747571
same thing for stocks; i did NOT receive tax receipts for the dec 30 sale due to settlement date of jan 4

$228k is this year's (2021) income even though the money was received in 2020
Yep. So the rules seem to say trade date, but I could not get the trade imported into Turbo Tax that had a settlement date in January the following year, and again, when I called Fidelity to complain, they explained that is how it works. I don't know why the discrepancy. All I know is that the government is still getting all their money in the end.... I didn't get my loss and overpaid in 2020. I'm ok as long as I get to take the 2020 loss this year, and tax my gains that settle in 2022 with my 2022 taxes.
 
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If you havent try out a good, professional tax person/company to help with your tax, I suggest you try it at least once.

I work in the game industry. When I found out a good tax guy that knows the in and out of my industry, he save me 10 of thousands of $$$. He would point out deduction/itemize that I didnt know about. Point out what is safe/not safe to claim, minimizing my tax burden and chances of audit.

Paid about $500 for the service, save about 10k -20k. ROI is roughly 3,000%

Now I need to find one that knows in and out of stocks/investing.
 
I have 12/31 750/950 at 94% profit. 12/31 700/900 at 95% profit. Today I opened 700/900 for Jan 7 that are already at 44% profit.
The only reason I'm not closing out the 12/31s and selling new spreads is because they contain the losses from rolls the week before. If I close them out now, I have $3M more income to pay taxes on for 2021. If I close them on 12/31, the profits counts as income in 2022 and I can wait to pay taxes until April 2023. I can make a lot of money on an extra $1.5M that is compounding over the next year.
For the Dec-31 sale, I am afraid you are required to pay advanced tax by April-2022. Advanced tax payments must be made quarterly for income that doesn’t have tax deductions like salary.
Hearty congratulations on your success with TSLA options!
 
For the Dec-31 sale, I am afraid you are required to pay advanced tax by April-2022. Advanced tax payments must be made quarterly for income that doesn’t have tax deductions like salary.
Hearty congratulations on your success with TSLA options!
Or what? You have to pay a less than 2% penalty when you file your taxes? Sounds like a cheap loan for ~12 months to me.
 
If you havent try out a good, professional tax person/company to help with your tax, I suggest you try it at least once.

I work in the game industry. When I found out a good tax guy that knows the in and out of my industry, he save me 10 of thousands of $$$. He would point out deduction/itemize that I didnt know about. Point out what is safe/not safe to claim, minimizing my tax burden and chances of audit.

Paid about $500 for the service, save about 10k -20k. ROI is roughly 3,000%

Now I need to find one that knows in and out of stocks/investing.

THIS

An excellent CPA will pay for themselves many MANY times over, each year.
 
well that was not very smart 😅 .
I had some small position 1055CCs left from last week that I flip rolled to 1010 puts for a small credit this morning when the stock hit 1025. I babysitted my 1080CCs and was ready to roll to next week if the squeeze got out of control. Then I sold some 1340 CCs for 31/12 since we are heading into Q4 earnings and FOMO herd is stampeding the ground. I am staying 30% OTM for now. Opened -p790 for 7/1. Back to wider positions I won’t manage for the next 2 weeks unless an Armageddon happens. Some time off with family before more time off next month. They just canceled my OR time for January and February because they are sending the OR nurses to the COVID ward since the number of cases skyrocketed +800% within 1 week. Gave my name to go help vaccinate when my OR time is cut. The fun part will be to flip roll some trades gone wrong between 2 shots.

Gave an Apple Watch to my wife because she wanted to record her training on Strava. Today she was working from home and she put the TSLA sticker on her watch so she could watch if the stock was approaching 1070 to trigger a roll for my 1080CCs next week when I was busy this afternoon. At least she is using that watch in a smart manner. :)

Today I learned to flip roll Covered calls into put. It was a small position but really an effective way to salvage a position going underwater. That’s exactly what I should have done with my AAPL Covered calls gone wrong. I guess we learn over time.
 
Good to see the message, was looking for someone with experience with penalty.
Did you deal with the penalty? Is it 2% on the taxes owed? Did IRS make any fuss over it, like asking for full review or something like that?
I had a small underpayment last year. I don't recall all of the details, but they was no audit, review, or anything. The penalty/interest is just on the underpayment amount, not on the full taxes owed for the year. (Though the calculation for the penalty can get complicated if you want to reduce it by claim uneven earnings for the year. Though I'm not sure it would be worth the effort.) And there are safe-harbors/outs where for example if you paid at least 110% of the tax that you owed last year you don't have to pay a penalty. (So I need to make sure to pay at least that much if I want to avoid the penalty this year.)
 
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May I suggest that those who want to discuss tax issues create a separate thread?
+1.

Tax is so nation-specific. For non-US citizens reading about IRA's and the like is the equivalent of the clutter in the main thread. Let's keep this thread pure options please. (We are doing a damn good job at staying on topic overall IMO).
 
Well, it was a quiet week for me. I opened some -750/650 BPS on the dip Monday with the SP in the upper 800s and expected to open more as the week went on, but with the big rally and short week I ended up sitting on the sidelines. I was able to close everything out yesterday at 95% profit.

I'm still not playing any BCS or CCs after getting burned during the Hertz week, As a result, I hit 50% of my weekly profit goal, but it was a stress free week (as far as trading) so no complaints.
 
Well, it was a quiet week for me. I opened some -750/650 BPS on the dip Monday with the SP in the upper 800s and expected to open more as the week went on, but with the big rally and short week I ended up sitting on the sidelines. I was able to close everything out yesterday at 95% profit.

I'm still not playing any BCS or CCs after getting burned during the Hertz week, As a result, I hit 50% of my weekly profit goal, but it was a stress free week (as far as trading) so no complaints.

I agree. I am going to get out of my covered calls on Monday and wait to see what happens until earnings. Hopefully the stock doesn't gap up a ton on Monday pre market so I can close all my calls for a relative small loss. Too bad I didn't think about closing them yesterday but this year has thought me that I need to trust my gut and that I should aggressively manage positions that I don't feel confident with.
 
I closed 12/31 820/600s in my son's account for >95% profit. Surprisingly little value for 12/31 900s. I'm confident on a production beat and 900 holding on 1/7. I will probably open 1/7 600/900s for him on Monday. Timing will depend on early price action - I'm hoping for a little dip to increase the values, at which point I might even drop back to 850s of premiums are good enough. After we hit the ER in later January, I will back away from chasing premiums and focus more on being >20% OTM for the spring time drop.
 
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