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Wiki Selling TSLA Options - Be the House

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You would be surprised how many people here still believe in MM manipulation.

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Maximizing Wash-Sale losses from 2023 against options gains in 2024

[EDIT: See responses that followed this post. This idea doesn't really work except for a narrow window of 30-days before and after the turn of the year, and can be helpful only in very specific circumstances.]

Been percolating on my mind and today I put it to action. Maybe some of you do this already, maybe it's obvious, maybe it's stupid and will turn out to be a waste of time, but sharing in case it can be useful to others:

1) I exported all trades I made in 2023 in CSV format from my broker and brought the file into Excel
2) Deleted all non-option trades (i.e., straight shares) and kept any option trades that had DTE in 2024-2026
2) Sorted by loss/gains and deleted all those with gains
3) Sorted by date and deleted all trades with an expiration before 1/1/24
4) Combined the remaining trades of the same DTE and made a total of losses for that strike/DTE
5) Saves a list of those positions and DTE

Often we forgot which trades they were and they disappear in the ether without us benefitting from the carry-forward of losses which offset new gains on the same contracts opened and closed in 2024.

I can give preference to these trades when the opportunity comes and enjoy gains against the carried-over losses.
 
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Sold 265 CCs for .10 (We have CPI, Elon chat and possible India Gujrat news ) ...

I sold Jan 25 500 Calls against all my shares, which is like .13c per week .... when you guys here are selling weekly calls .. how much are you expecting to bank ... what would be the average?
$0.50 to $0.80 on 10-11 DTE CC at 10%-12% OTM recently.
 
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Sold 265 CCs for .10 (We have CPI, Elon chat and possible India Gujrat news ) ...

I sold Jan 25 500 Calls against all my shares, which is like .13c per week .... when you guys here are selling weekly calls .. how much are you expecting to bank ... what would be the average?
A hell of a lot more that that!
 
Maximizing Wash-Sale losses from 2023 against options gains in 2024

💡

Been percolating in my mind and today I put it to action. Maybe some of you do this already, but sharing in case it can be useful to others:

1) I exported all trades I made in 2023 in CSV format from my broker and brought the file into Excel
2) Deleted all non-option trades (i.e., straight shares) and kept any option trades that had DTE in 2024-2026
2) Sorted by loss/gains and deleted all those with gains
3) Sorted by date and deleted all trades with an expiration before 1/1/24
4) Combined the remaining trades of the same DTE and made a total of losses for that strike/DTE
5) Saves a list of those positions and DTE

Now I have a list of options I can re-use in 2024, when they make sense obviously, and any gains on them will be tax-free, since I took the losses last year and wash-sale rules carries the losses over against gains on the same trade in the new year (here 2024). Often we forgot which trades they were and they disappear in the ether without us benefitting from the carry-forward of losses which offset new gains on the same contracts opened and closed in 2024.

For me that came to this list below which seems very doable. I can give preference to these trades when the opportunity comes and enjoy gains against the carried-over losses.

If I'm missing something in this thought-process please let me know!

My resulting list of 2023 wash-sale positions with carried over "credits" into 2024

+C230 1/19/24
-C270 1/19/24

-C250 3/15/24
-C280 3/15/24
-C300 3/15/24

-C300 6/21/24

-C300 9/20/24

+C150 12/19/25
-P300 12/19/25
-C450 12/19/25

+C300 1/16/26

If you took losses in 2023 on them, why do you have to open the same contract? Any extra capital loss carries forward and will cancel out any capital gain regardless of what the option is.

And if you do resell the same contract you took a loss on in 2023 within 30 days, then that will remove those capital losses from 2023 and put it into the cost basis of the new open position. After 30 days, it’s just a fresh new position.
 
A hell of a lot more that that!
Oh Yeah, but I get better sleep :) and I need to manage less ... auto pilot. I guess it's more like dividends ..
+Can you put all your shares on the line every week? Mine are for all shares .. quantity over quality ;)

One year average across all conditions ..

Selling CCs when SP is too low ... asking for trouble on a reversal ...
Looks like I am at .02-0.04 delta for the year, and you all are doing .1 to 0.08 deltas with more knowledge and info to process ...

Down the road I might do more monthlies/weeklies ... right now weeklies only on shares I wanna sell and some Calls from piggy bank... cheers!!
 
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If you took losses in 2023 on them, why do you have to open the same contract? Any extra capital loss carries forward and will cancel out any capital gain regardless of what the option is.

I thought Wash-Sale losses are tied to specific contracts that incurred the loss. Are you saying all losses from one year globally carry into the next against gains? I don't think so, unless I'm missing something.

And if you do resell the same contract you took a loss on in 2023 within 30 days, then that will remove those capital losses from 2023 and put it into the cost basis of the new open position. After 30 days, it’s just a fresh new position.

Correct re the 30 days. I realize that now, I ended 2023 with -$1,900 or so realized gains with wash sales applied, and I checked today and it changed to +$8,566, apparently since I churned some of the same contracts in 2024 within 30 days and those gains/losses were indeed disallowed (I don't mind really).

I guess then this works if one waits 30-days and then re-uses those positions. I say this because, for example, I STO last week -C300 3/2024 at X price and overnight it changed the STO price to a negative number (“reducing” taxable gains) since I held the same position in 2023 and closed then for a loss (for whatever reason) which then carried forward into 2024. So I know there's internal calculations going on behind the scenes from the broker and I'm looking to maximize the benefits if I can.
 
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I thought Wash-Sale losses are tied to specific contracts that incurred the loss. Are you saying all losses from one year globally carry into the next against gains? I don't think so, unless I'm missing something.



Correct re the 30 days. I realize that now, I ended 2023 with -$1,900 or so realized gains with wash sales applied, and I checked today and it changed to +$8,566, apparently since I churned some of the same contracts in 2024 within 30 days and those gains/losses were indeed disallowed (I don't mind really).

I guess then this works if one waits 30-days and then re-uses those positions. I say this because, for example, I STO last week -C300 3/2024 at X price and overnight it changed the STO price to a negative number (“reducing” taxable gains) since I held the same position in 2023 and closed then for a loss (for whatever reason) which then carried forward into 2024. So I know there's internal calculations going on behind the scenes from the broker and I'm looking to maximize the benefits if I can.

Edit: I opened a few just now as an experiment, to see tomorrow if the broker adjusts the prices downward for those that were closed more than 30 days ago. The last column on the right is the price I paid/got for them:

View attachment 1007161
And remember, it’s really more like a 60/61 day rule..since it starts BEFORE the actual sale of the security (that creates the loss) and then AFTER the sale…

options wash sale rules make this more difficult to track, and what I can’t tell you is if the “similar” means AN TSLA OPTION, or must it be the same strike and expiry, or same expiry, or same strike but different expiry?
 
And remember, it’s really more like a 60/61 day rule..since it starts BEFORE the actual sale of the security (that creates the loss) and then AFTER the sale…

options wash sale rules make this more difficult to track, and what I can’t tell you is if the “similar” means AN TSLA OPTION, or must it be the same strike and expiry, or same expiry, or same strike but different expiry?
It varies from broker to broker. Before doing any kind of option tax loss harvesting, better to call your broker and find out what their algorithm does. I found out from IBKR that they treated "substantially identical" in a narrowest of sense, meaning same strike same exp. So I sold all of my swing shares late 2022 and bought +5C's exp late March 2023, realizing a substantial tax loss which covered all of my option gains in 2023 and a big chunk still remains for 2024. My unrealized gain for 2023 since exercising those +5C's is massive though.
 
I thought Wash-Sale losses are tied to specific contracts that incurred the loss. Are you saying all losses from one year globally carry into the next against gains? I don't think so, unless I'm missing something.



Correct re the 30 days. I realize that now, I ended 2023 with -$1,900 or so realized gains with wash sales applied, and I checked today and it changed to +$8,566, apparently since I churned some of the same contracts in 2024 within 30 days and those gains/losses were indeed disallowed (I don't mind really).

I guess then this works if one waits 30-days and then re-uses those positions. I say this because, for example, I STO last week -C300 3/2024 at X price and overnight it changed the STO price to a negative number (“reducing” taxable gains) since I held the same position in 2023 and closed then for a loss (for whatever reason) which then carried forward into 2024. So I know there's internal calculations going on behind the scenes from the broker and I'm looking to maximize the benefits if I can.

Edit: I opened a few just now as an experiment, to see tomorrow if the broker adjusts the prices downward for those that were closed more than 30 days ago. The last column on the right is the price I paid/got for them:

View attachment 1007161

Yes, I'm fairly certain all capital losses carry globally into the next year against all capital gains.

I think the reason the STO price changed to a negative number is because selling it means you washed the 2023 loss of that option and that loss is now part of the cost basis of the new contract.

Edit: You might be able to confirm this by comparing the amount of the 2023 loss-to-gain change with the adjusted cost basis of the new options you opened less than 30 days after closing them. They should be the same amount.
 
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Oh Yeah, but I get better sleep :) and I need to manage less ... auto pilot. I guess it's more like dividends ..
+Can you put all your shares on the line every week? Mine are for all shares .. quantity over quality ;)

One year average across all conditions ..

Selling CCs when SP is too low ... asking for trouble on a reversal ...
Looks like I am at .02-0.04 delta for the year, and you all are doing .1 to 0.08 deltas with more knowledge and info to process ...

Down the road I might do more monthlies/weeklies ... right now weeklies only on shares I wanna sell and some Calls from piggy bank... cheers!!
OK, I'll bite... if I had 10000 TSLA and a similar value in cash, then I would be writing 100x -p & -c each week for $1 premium, that's my end-game
 
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Yes, I'm fairly certain all capital losses carry globally into the next year against all capital gains.

I think the reason the STO price changed to a negative number is because selling it means you washed the 2023 loss of that option and that loss is now part of the cost basis of the new contract.

Edit: You might be able to confirm this by comparing the amount of the 2023 loss-to-gain change with the adjusted cost basis of the new options you opened less than 30 days after closing them. They should be the same amount.

Okay, turns out I got excited for nothing (or for very little :cool:) but I learned something in the process.

I just spoke with my broker (TD Ameritrade) and they said only trades from 11/30/23 onward will have any effect on the equivalent trades in 2024 and those will end on 1/31/24 as well (~60 day straddle). So I was wrong to assume losses taken last year in say, March, can help offset gains this year by TD internally changing its specific cost basis.

Plus they explained that wash sale isn't "free money" and just pushes the gain or loss back to 2023 or forward in 2024 (like a squishy pillow), so all the work isn't really necessary unless I have specific heavy gains/losses in 2023 to take advantage of and open new contracts at different strikes in 2024 to offset them (like @dl003 did).

Also TD counts contracts 1:1 for wash sales, not globally any options for any options.

I guess I can delete my original post but maybe I'll leave up in case the question comes up again for someone else.
 
OK, have been busy, hard work, callouses...

Rolled my 65x Dec 2025 +p270's to June 2026*

Rolled down 59x Sep 2024 -p300 to -p270 (now have 65x), formed a straddle, STO 59x -c270 (now have 65x)

*actually didn't finish the roll yet, still holding the 65x Dec 2025 +p270 and have a choice - I can keep them in case of a drop, or sell them and recuperate my cash, it's $460k's worth... or maybe sell 35x and play with 30x, yes maybe that's a sound strategy...

Edit: decided not to create extra risk and put in a limit sell -> Anyway, mission completed, +6 months on the puts almost for free and from a -p300 to a -270 straddle, way lower risk for more premium
 
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Went on 7x +187.5C last week on AAPL. Made double the investment from today pump.

For those that have not followed Wicked, he provide great daily updates on Youtube for AAPL and TSLA, which Jim baked into his daily charts.

Back to Tesla - going wait till near end of Thursday to placed that butterfly.

ICs still going strong at -235p and -260c

Depend on how strong we head into CPI may close early. Risk Management
 
Nice! This seems to imply wait for $250-$253 before selling calls, or scale in slowly as SP rises, perhaps -C300 6/21/24.
Correct?
I don't know how high this dead cat can go. Depending on the news I guess, but I know it's a dead cat. So just stick to intraday resistance to sell 257.5+.
 
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